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A stereoselective synthesis of the azaspiboundecane ring system of (−)-histrionicotoxin from (+)-glutamic acid

✍ Scribed by Jeffrey D. Winkler; Paul M. Hershberger; James P. Springer

Book ID
104219241
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
215 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 three of the four chiral centers in (-)-histrioniootoxin.

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