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

Org Biomol Chem

Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune, 411 008, India.

Published: December 2011

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.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c1ob06320kDOI Listing

Publication Analysis

Top Keywords

asymmetric total
8
total syntheses
8
absolute configuration
8
oxazinin-5 oxazinin-6
8
oxazinin-6 preoxazinin-7
8
syntheses assignment
4
assignment absolute
4
configuration oxazinin-5
4
preoxazinin-7 asymmetric
4
syntheses unprecedented
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!