Asymmetric first total syntheses and assignment of absolute configuration of oxazinin-5, oxazinin-6 and preoxazinin-7

TitleAsymmetric first total syntheses and assignment of absolute configuration of oxazinin-5, oxazinin-6 and preoxazinin-7
Publication TypeJournal Article
Year of Publication2011
AuthorsDethe, DH, Ranjan, A, Pardeshi, VH
JournalOrganic & Biomolecular Chemistry
Volume9
Issue23
Pagination7990-7992
Date PublishedSEP
ISSN1477-0520
Abstract

Asymmetric first total syntheses of the unprecedented toxins oxazinin-5, oxazinin-6 and preoxazinin-7 have been achieved from a common key intermediate 18, derived from a regiocontrolled Sharpless asymmetric aminohydroxylation and oxa-Michael reaction, which in addition to confirming the structure also established the absolute configuration of the natural products. On the way an expeditious synthesis of a metabolite bursatellin was completed in 8 steps.

DOI10.1039/c1ob06320k
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.85
Divison category: 
Organic Chemistry