JPS5833858B2 - Method for producing sesquiterpene derivatives - Google Patents
Method for producing sesquiterpene derivativesInfo
- Publication number
- JPS5833858B2 JPS5833858B2 JP3557280A JP3557280A JPS5833858B2 JP S5833858 B2 JPS5833858 B2 JP S5833858B2 JP 3557280 A JP3557280 A JP 3557280A JP 3557280 A JP3557280 A JP 3557280A JP S5833858 B2 JPS5833858 B2 JP S5833858B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- structural formula
- compound represented
- producing
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000004354 sesquiterpene derivatives Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- 230000001590 oxidative effect Effects 0.000 claims 3
- 229930004725 sesquiterpene Natural products 0.000 claims 2
- 230000000397 acetylating effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- -1 diacetoxy-furan compound Chemical class 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- QGMWDUUHVVLHNP-AEGPPILISA-N Warburganal Chemical compound C[C@@]1([C@@](C(C=O)=CC2)(O)C=O)[C@@H]2C(C)(C)CCC1 QGMWDUUHVVLHNP-AEGPPILISA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- QGMWDUUHVVLHNP-UHFFFAOYSA-N Warburganal Natural products C1C=C(C=O)C(C=O)(O)C2(C)C1C(C)(C)CCC2 QGMWDUUHVVLHNP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明は、構造式： で表わされる化合物の新規な製法に関するものである。[Detailed description of the invention] The present invention has the structural formula: The present invention relates to a novel method for producing a compound represented by:
本発明の目的化合物は、夜盗蛾（ａｒｍｙｗｏｒｍ）に
対して強力な摂食阻止物質
（ａｎｔｉｆｅｅｄａｎｔ ）作用を示す天然物として
すでに単離されているバーバーガナー／Ｌ／ （Ｗａｒ
ｂｕｒｇａｎａｌ）ＣＣｈｅｍ、Ｃｏｍｍ０、Ｐ、１０
１３（１９７６））に変換する際の重要な中間体として
有用なものである。The object compound of the present invention is Barberganer/L/ (War
burganal)CChem,Comm0,P,10
13 (1976)).
上記バーバーガナールは、すでに、本発明者らにより、
β−ヨノン（β−１ｏｎｏｎｅ ）を出発物質として、
イソトリメニンを経由して全合成が完成されている（特
願昭５３−１１０３５６号、同５３−１１０３５７号、
同５３−１１０３５８号、同５３−１１０３５９号、同
５３−１１０３６０号、同５４−４２３１４号、同５４
−４２３１６号参照）。The above Barbaganal has already been developed by the present inventors.
Using β-ionone (β-1onone) as a starting material,
Total synthesis has been completed via isotrimenine (Japanese Patent Application No. 53-110356, No. 53-110357,
No. 53-110358, No. 53-110359, No. 53-110360, No. 54-42314, No. 54
-42316).
本発明者らは、前記工程の改良について更に鋭意研究を
行った結果、前記工程中における化合物（１２）を出発
物質として、化合物（１９）を更に短工程かつ収率よく
得る方法を見出し、本発明を完成するに至った。As a result of further intensive research into improving the above process, the present inventors discovered a method for obtaining compound (19) in a shorter process and with higher yield using compound (12) in the above process as a starting material. The invention was completed.
すなわち、前記工程においては、化合物（１２）から化
合物（１９）を得るためには７エ程という多くの工程を
要するが、本発明によれば、わずか３工程で得ることが
できる。That is, in the above steps, as many as 7 steps are required to obtain compound (19) from compound (12), but according to the present invention, compound (19) can be obtained in only 3 steps.
以下に、本発明を説明する。The present invention will be explained below.
まず、出発物質のジアセトキシ−フラン体（１２）を還
元剤で処理して、還元とフラン環の開裂を行って、ジオ
ール体Ａを高収率で得る。First, diacetoxy-furan compound (12) as a starting material is treated with a reducing agent to perform reduction and cleavage of the furan ring, thereby obtaining diol compound A in high yield.
上記反応において、還元剤としては、水素化リチウムア
ルミニウムが最適であり、溶媒としては例工ばエーテル
、ジオキサン、テトラヒドロフラン等のエーテル類が好
適である。In the above reaction, lithium aluminum hydride is most suitable as the reducing agent, and ethers such as ether, dioxane, and tetrahydrofuran are suitable as the solvent.
この反応は、まず水冷下で約０．５〜１時間反応＊＊を
行った後、室温で約４〜１２時間行うのがよい。This reaction is preferably carried out for about 0.5 to 1 hour under water cooling, and then for about 4 to 12 hours at room temperature.
得られたジオール体（４）をアセチル化するとジアセト
キシ体（Ｂ）が高収率で得られる。When the obtained diol compound (4) is acetylated, diacetoxy compound (B) is obtained in high yield.
この際、アセチル化剤としては、例えば無水酢酸−上リ
ンクや塩化アセチルを用いるのが好適である。In this case, as the acetylating agent, it is preferable to use, for example, acetic anhydride or acetyl chloride.
この反応は、溶媒中にジオール体（Ａ）を溶解し、約Ｏ
〜２５℃で約４〜１２時間放置することにより好適に進
行する。This reaction involves dissolving the diol (A) in a solvent, and approximately O
The process is preferably carried out by standing at ~25°C for about 4 to 12 hours.
得られたジアセトキシ体（Ｂ）を酸化して、目的化合物
のジアセトキシ−オキソ体０９）を収率よく得ることが
できる。The obtained diacetoxy compound (B) is oxidized to obtain the target compound diacetoxy-oxo compound 09) in good yield.
上記反応において、酸化剤としては、Ｃｒ０３−酢酸が
最適であり１１反反応度及び反応時間は、それぞれ室温
、約３〜１２時間で充分反応は進行する。In the above reaction, Cr03-acetic acid is most suitable as the oxidizing agent, and the reaction proceeds sufficiently at room temperature and about 3 to 12 hours, respectively.
本発明の工程を化学式に示せば次の如（である。The process of the present invention can be expressed as a chemical formula as follows.
以下に、１本発明を実施例により更に具体的に説明する
。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例
■
化合物（１２）３３６ｍ９をエーテ）’Ｉｙ３０ｍ１．
に溶かし水素化リチウムアルミニウム１９０■を加え、
水冷下１時間、室温で１時間攪拌後、氷冷し、水、１０
％塩酸を加え、エーテル層を飽和炭酸水素ナトリウム水
溶液、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥後
溶媒を留去し、得られた結晶をエーテル・ヘキサンから
再結晶した。Example ■ Compound (12) 336m9 was converted to ether)'Iy30m1.
Add 190cm of lithium aluminum hydride dissolved in
After stirring for 1 hour under water cooling and 1 hour at room temperature, cool on ice, add water, 10
% hydrochloric acid was added, and the ether layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, and the solvent was distilled off. The resulting crystals were recrystallized from ether/hexane.
化合物（４）の無色結晶（ｍ、ｐ、： ｓ３〜８５’ｃ
）が２１４■（収率９０％）が得られた。Colorless crystals of compound (4) (m, p,: s3-85'c
) was obtained, 214 ■ (yield 90%).
元素分析：（Ｃｌ５Ｈ２６０２として）
計算値： Ｃ，７５，５８；Ｈ，１０，９９実測値：Ｃ
，７５，６５；Ｈ，１０，７２ＣＣ１４−１゜
■、Ｒ６ν α 、３３００
ａＸ
Ｎ、Ｍ、 Ｒ，（ＣＤＣｌ３．１００ＭＨｚ）：δ０．
８１ （３Ｈ，ｓｌＭｅ ）、０．８８（３Ｈ。Elemental analysis: (as Cl5H2602) Calculated value: C, 75,58; H, 10,99 Actual value: C
,75,65;H,10,72CC14-1゜■, R6ν α, 3300 aX N, M, R, (CDCl3.100MHz): δ0.
81 (3H, slMe), 0.88 (3H.
ｓ、Ｍｅ）、０．９７ （３Ｈ，ｓ、 Ｍｅ ）、２．
１〜２．３ （２Ｈ，ｍ ）、３．９〜４．３ （４Ｈ
，ｍ ）。s, Me), 0.97 (3H, s, Me), 2.
1-2.3 (2H, m), 3.9-4.3 (4H
, m).
実施例 ２
化合物（Ａ）６１４７Ｑをピリジン５−に溶かし、無水
酢酸５ｍＡ’を加え冷蔵庫中に一晩放置し、水を加え過
剰の無水酢酸を分解した後、エーテル抽出し、エーテル
層を５％塩酸、１０％炭酸ナトリウム水溶液、飽和食塩
水で洗浄し、硫酸マグネシウムで乾燥し、溶媒を留去後
シリカゲルカラムクロマトグラフィーに付すとヘキサン
：酢酸エチル（１０：１）の溶出部から油状物の化合物
（Ｂ）が７６９■（収率８９％）得られた。Example 2 Compound (A) 6147Q was dissolved in pyridine 5-, 5 mA' of acetic anhydride was added, and the mixture was left overnight in the refrigerator. After water was added to decompose excess acetic anhydride, it was extracted with ether, and the ether layer was reduced to 5% Washing with hydrochloric acid, 10% aqueous sodium carbonate solution, and saturated brine, drying over magnesium sulfate, distilling off the solvent, and subjecting to silica gel column chromatography yielded an oily compound from the hexane:ethyl acetate (10:1) eluate. 769 μ of (B) was obtained (yield: 89%).
質量分析： （Ｃ１９Ｈ３００４として）ｍ／ｅ ：
３２２ （Ｍ＋）、２６２（Ｍ＋Ａｃ０Ｈ）
１、Ｒ，・ＣＨＣｌ３−１：１７３０
ａＸ
Ｎ１Ｍ、Ｒ，（ＣＤＣ１３，１００ＭＨｚ）：δ０．８
５ （３Ｈ，ｓ、 Ｍｅ ）、０．９０（３Ｈ。Mass spectrometry: (as C19H3004) m/e:
322 (M+), 262 (M+Ac0H) 1, R, ・CHCl3-1: 1730 aX N1M, R, (CDC13, 100 MHz): δ0.8
5 (3H,s, Me), 0.90 (3H.
ｓ、Ｍｅ）、０．９９（３Ｈ１８、Ｍｅ ）、２．０１
（３Ｈ，ｓ、 ＯＡｃ ）、２．０３（３Ｈ。s, Me), 0.99 (3H18, Me), 2.01
(3H,s, OAc), 2.03 (3H.
ｓ、 ＯＡｃ ）、４．４６ （ＩＨ，ｄ、 ｊ＝
１２Ｈｚ ）、４．５９ （２Ｈ，ｓ ）、４．６３（
ＬＨ。s, OAc), 4.46 (IH, d, j=
12Hz), 4.59 (2H,s), 4.63(
LH.
ｄ、ｊ＝１２Ｈｚ ）。d, j = 12Hz).
実施例 ３
化合物（Ｂ）７６９■を酢酸細ｌに溶かし無水クロム酸
７１７ｒＩＴ９を加え室温で一晩攪拌する。Example 3 Compound (B) 769■ was dissolved in a thin liter of acetic acid, chromic anhydride 717rIT9 was added, and the mixture was stirred overnight at room temperature.
反応抜水を加えエーテル抽出し、エーテル層を飽和炭酸
水素ナトリウム、飽和食塩水で洗浄、硫酸マグネシウム
で乾燥後、溶媒を留去しシリカゲルカラムクロマトグラ
フィーに付すとヘキサン：酢酸エチル（４：１）の溶出
部から化合物（１９）が５０７■（収率６３％）得られ
た。Drained reaction water was added and extracted with ether. The ether layer was washed with saturated sodium bicarbonate and saturated brine, dried over magnesium sulfate, the solvent was distilled off and subjected to silica gel column chromatography to obtain hexane:ethyl acetate (4:1). From the eluted portion, 507 ml of compound (19) (yield 63%) was obtained.
これをエーテル・ヘキサンから再結晶すると無色針状晶
（ｒｎ、ｐ、：８７〜８８℃）が得られた。When this was recrystallized from ether/hexane, colorless needle crystals (rn, p,: 87-88°C) were obtained.
元素分析： （Ｃ１９Ｈ２Ｓ ０５ として）計算値：
Ｃ，６７，８３；Ｈ，８，３９実測値：Ｃ，６７，８
９；Ｈ２Ｓ、３６
１、Ｒ，シＣＣｌ４−１：１７４５．１６８０Ｃ品
ａＸ
Ｎ、Ｍ、 Ｒ，（ＣＤＣｌ３．１００ＭＥ（ｚ ） ：
δ０．９１ （３Ｈ，ｓ、 Ｍｅ ）、０．９４（３Ｈ
１ｓＳＭｅ）、１．１８ （３Ｈ，ｓ、 Ｍｅ ）、２
．００ （３Ｈ，ｓ、 ＯＡｃ ）、２．０５（３Ｈ
。Elemental analysis: Calculated value (as C19H2S 05):
C, 67,83; H, 8, 39 Actual value: C, 67, 8
9; H2S, 36 1, R, CCl4-1:1745.1680C product aX N, M, R, (CDCl3.100ME(z):
δ0.91 (3H,s, Me), 0.94 (3H
1sSMe), 1.18 (3H,s, Me), 2
．． 00 (3H, s, OAc), 2.05 (3H
.
ｓ、ＯＡｃ ）。s, OAc).
Claims (1)
ペン誘導体の製法。 ２ 構造式： で表わされる化合物をアセチル化して、構造式：で表わ
される化合物を得、 して、構造式： さらに該化合物を酸化 で表わされる化合物を得るこ キテルペン誘導体の製法。 ３ 構造式： とを特徴とするセス で表わされる化合物を還元、開環を行って、構造式： で表わされる化合物を得、該化合物をアセチル化して、
構造式： で表わされる化合物を得、 して、構造式： さらに該化合物を酸化 で表わされる化合物を得ることを特徴とするセスキテル
ペン誘導体の製法。[Scope of Claims] 1. A method for producing a sesquiterpene derivative, which comprises oxidizing a compound represented by the structural formula: to obtain a compound represented by the structural formula: 2. A method for producing a chiterpene derivative, which comprises acetylating a compound represented by the structural formula to obtain a compound represented by the structural formula; and further oxidizing the compound to obtain a compound represented by the structural formula. 3 A compound represented by the structural formula: is reduced and ring-opened to obtain a compound represented by the structural formula: and the compound is acetylated,
A method for producing a sesquiterpene derivative, which comprises obtaining a compound represented by the structural formula: and further oxidizing the compound to obtain a compound represented by the structural formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3557280A JPS5833858B2 (en) | 1980-03-19 | 1980-03-19 | Method for producing sesquiterpene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3557280A JPS5833858B2 (en) | 1980-03-19 | 1980-03-19 | Method for producing sesquiterpene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56131547A JPS56131547A (en) | 1981-10-15 |
| JPS5833858B2 true JPS5833858B2 (en) | 1983-07-22 |
Family
ID=12445466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3557280A Expired JPS5833858B2 (en) | 1980-03-19 | 1980-03-19 | Method for producing sesquiterpene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5833858B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0671357U (en) * | 1993-03-23 | 1994-10-07 | 住友金属工業株式会社 | Driving force transmission device for railway vehicles |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5235098A (en) * | 1987-06-23 | 1993-08-10 | Basf K&F Corporation | Method for preparing dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and novel haloethyl decalin derivatives |
-
1980
- 1980-03-19 JP JP3557280A patent/JPS5833858B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0671357U (en) * | 1993-03-23 | 1994-10-07 | 住友金属工業株式会社 | Driving force transmission device for railway vehicles |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56131547A (en) | 1981-10-15 |
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