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Stereocontrolled synthesis of the histrionicotoxin ring system

โœ Scribed by David Tanner; Peter Somfai

Book ID
104222468
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
229 KB
Volume
26
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Two simple, efficient and stereocontrolled routes to the cisazaspiro-L5.5]-undecan-E-01 skeleton of the histrionicotoxin alkaloids are described.

Histrionicotoxin, I, is an unusual alkaloid isolatedlf2 from extracts of

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A stereoselective synthesis of the azasp
A stereoselective synthesis of the azaspiboundecane ring system of (โˆ’)-histrionicotoxin from (+)-glutamic acid
โœ Jeffrey D. Winkler; Paul M. Hershberger; James P. Springer ๐Ÿ“‚ Article ๐Ÿ“… 1986 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 215 KB

We describe herein the first stereoselective synthesis of the natural (-)-histrionicotoxin ring system, where the chirality is derived from L-glutamic acid. The key transformation involves intramolecular dioxolenone photocycloaddition of a substrate derived from the amino acid, which establishes thr