Issue 37, 2014

Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step

Abstract

A divergent, short, and novel total synthesis of 1,6,8a-tri-epi-castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed via a common precursor, 15, obtained from D-mannitol derived β-lactam. The key step involves a one pot cascade sequence of trimethyl sulfoxonium ylide based cyclization of epoxy sulfonamide 14via epoxide ring opening, one carbon homologation followed by intramolecular cyclization.

Graphical abstract: Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step

Supplementary files

Article information

Article type
Paper
Submitted
08 May 2014
Accepted
30 Jul 2014
First published
31 Jul 2014

Org. Biomol. Chem., 2014,12, 7389-7396

Author version available

Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step

D. K. Tiwari, K. C. Bharadwaj, V. G. Puranik and D. K. Tiwari, Org. Biomol. Chem., 2014, 12, 7389 DOI: 10.1039/C4OB00948G

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