Alkynyliodonium Salts in Organic Synthesis. Application to the Preparation of the Tricyclic Core of (±)-Halichlorine

The tricyclic core of halichlorine has been synthesized through the use of an alkynyliodonium salt/alkylidenecarbene/1,5 C−H insertion sequence that sets the pivotal quaternary center in the target.

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Bibliographic Details
Published in:Journal of organic chemistry 2004-11, Vol.69 (23), p.7928-7932
Main Authors: Feldman, Ken S, Perkins, Angela L, Masters, Katherine M
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Onium Compounds - chemistry
Organic chemistry
Preparations and properties
Salts - chemistry
Spiro Compounds - chemical synthesis
Stereoisomerism
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Description
Summary:The tricyclic core of halichlorine has been synthesized through the use of an alkynyliodonium salt/alkylidenecarbene/1,5 C−H insertion sequence that sets the pivotal quaternary center in the target.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0487911