Construction of the tricyclic core of the marine alkaloid sarain A

The alkaloidal nucleus of sarain A (1) has been synthesized by a short route involving a [3 + 2] azomethine ylide cycloaddition and an allysilane/N-sulfonyliminium ion cyclization as key steps.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 56; no. 10; pp. 3210 - 3211
Main Authors Sisko, Joseph, Weinreb, Steven M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.05.1991
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ELECTROORGANIC CHEMISTRY
CONCISE ENANTIOSELECTIVE SYNTHESIS
ACID
PYRROLIDINES
AMIDES
Organic cation
Sulfonamide
Cyclization
Nitrogen heterocycle
Iminium compounds
Organic silane
Tricyclic compound
Allylic compound
Azomethine ylide
Dipolar cycloaddition
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Summary:The alkaloidal nucleus of sarain A (1) has been synthesized by a short route involving a [3 + 2] azomethine ylide cycloaddition and an allysilane/N-sulfonyliminium ion cyclization as key steps.
Bibliography:istex:E13E702845ECDD1BDB0BDCF82B40234E78765841
ark:/67375/TPS-65HPKTXQ-5
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00010a006