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

Autor:	Jeffrey D. Winkler, James P. Springer, Paul M. Hershberger
Rok vydání:	1986
Předmět:	inorganic chemicals chemistry.chemical_classification Chemistry Stereochemistry organic chemicals Organic Chemistry Glutamic acid Ring (chemistry) Biochemistry Amino acid Intramolecular force Drug Discovery Stereoselectivity Enantiomer Chirality (chemistry) Lactone
Zdroj:	Tetrahedron Letters. 27:5177-5180
ISSN:	0040-4039
Popis:	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 (−)-histrionicotoxin.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::798f5263b2d684d75b07069fade8843d https://doi.org/10.1016/s0040-4039(00)85162-x Zobrazit plný text záznamu