Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B

The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium salt → alkylidenecarbene → cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subseq...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-10, Vol.67 (20), p.7096-7109
Main Authors: Feldman, Ken S, Saunders, Joe C, Wrobleski, Michelle Laci
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkynes - chemistry
Animals
Chemistry
Combinatorial Chemistry Techniques
Cyclopentanes - chemical synthesis
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Oxazolidinones - chemical synthesis
Porifera - chemistry
Preparations and properties
Salts - chemistry
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Summary:The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium salt → alkylidenecarbene → cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026287v