[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

Michael et al., 1998 - Google Patents

An expeditious synthesis of the dendrobatid indolizidine alkaloid 167B

Michael et al., 1998

Document ID
9686576106678663697
Author
Michael J
Gravestock D
Publication year
Publication venue
European journal of organic chemistry

External Links

Snippet

The synthesis of the racemic title alkaloid 1 has been accomplished in eight steps and 7.2% overall yield from pyrrolidine‐2‐thione (5) and ethyl hex‐2‐enoate (6). Key steps include a ring closure that takes advantage of the nucleophilicity of a vinylogous urethane 8, and …
Continue reading at chemistry-europe.onlinelibrary.wiley.com (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring heteroatom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals substituted by singly or doubly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings

Similar Documents

Publication Publication Date Title
Overman et al. Synthesis applications of aza-Cope rearrangements. Part 10. A new approach for the total synthesis of pentacyclic Aspidosperma alkaloids. Total synthesis of dl-16-methoxytabersonine
Liu et al. Oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine
SU511005A3 (en) The method of obtaining (methoxymethylfurylmethyl) 6,7-benzomorfan or morphinan
White et al. Structure, Sythesis and Absolute Configuration of Leptosphaerin, a Metabolite of the Marine Ascomycete Leptosphaeria oraemaris.
Michael et al. An expeditious synthesis of the dendrobatid indolizidine alkaloid 167B
Xiong et al. An efficient asymmetric route to eudesmane acids. Total synthesis of (+)-12-hydroxy-α-cyperone,(+)-12-oxo-α-cyperone and (+)-3-oxoeudesma-4, 11 (13)-dien-12-oic acid
Tanaka et al. Total syntheses of the lignans isolated from Schisandra Chinensis
Ponpandian et al. Sequential deprotection–Cyclisation reaction: Stereoselective synthesis of azabicyclic β-enamino ester derivatives and (−) indolizidine 209D
Craven et al. Cytochalasan syntheses: Synthesis of (17S, 18S)-17, 18-dihydroxy-10-(prop-2-YL)-14-methyl-[11] cytochalasa-6 (7), 13z, 19E-triene-1, 21-dione; an isomer of aspochalasin C
Barker et al. Synthesis of tricyclic analogues of methyllycaconitine using ring closing metathesis to append a B ring to an AE azabicyclic fragment
Niwa et al. Total synthesis of optically active integerrimine, a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type
Mash et al. Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-. beta.-eudesmol
Chrzanowska et al. Asymmetric synthesis of (R)-(+)-and (S)-(−)-2, 3-methylenedioxy-8-oxoberbine (gusanlung D)
Högermeier et al. Nonaflates from 8‐Oxabicyclo [3.2. 1] oct‐6‐en‐3‐ones as Building Blocks for Diversity‐Orientated Synthesis: Preparation, Heck‐Couplings and Subsequent Diels–Alder Reactions
DE19755480A1 (en) Substituted heterocyclic benzocycloalkenes and their use as analgesic substances
Barluenga et al. [8+ 2] and [8+ 3] Cyclization Reactions of Alkenyl Carbenes and 8‐Azaheptafulvenes: Direct Access to Tetrahydro‐1‐azaazulene and Cyclohepta [b] pyridinone Derivatives
Zambrano et al. Asymmetric total synthesis of 1-deoxy-7, 8-di-epi-castanospermine
Yoshida et al. Synthesis of granulatimide positional analogues
Wattanasin et al. Stereocontrolled synthesis of cis-fused hydroisoquinolines by an intramolecular Diels-Alder reaction of (Z)-dienes
Solladie et al. Asymmetric Synthesis of (2R, 5S, 7R)-2, 7-Dimethyl-1, 6-dioxaspiro [4.4] nonane
Burtoloso et al. Asymmetric synthesis of cis-2, 4-disubstituted azetidin-3-ones from metal carbene chemistry
Michael, Joseph P.* & Gravestock An enantioselective synthesis of (-)-indolizidine 167B, a skin alkaloid from a neotropical dendrobatid frog
Macías et al. A stereoselective route towards heliannuol A
Müller et al. Alkoxycarbonylcarbene transfer to semicyclic enaminones–a route to cyclopenta [b] pyrrole and indole ring systems
Jousse et al. A New Approach to Erythrinanes through Pummerer‐Type Cyclization