Synthesis of the macrocyclic core of iriomoteolide 3a

Chada Raji Reddy; Gajula Dharmapuri; Nagavaram Narsimha Rao

doi:10.1021/ol9025183

Synthesis of the macrocyclic core of iriomoteolide 3a

Org Lett. 2009 Dec 17;11(24):5730-3. doi: 10.1021/ol9025183.

Authors

Chada Raji Reddy¹, Gajula Dharmapuri, Nagavaram Narsimha Rao

Affiliation

¹ Organic Division-I, Indian Institute of Chemical Technology, Hyderabad, India 500 007. rajireddy@iict.res.in

PMID: 19928780
DOI: 10.1021/ol9025183

Abstract

The asymmetric synthesis of the fully functionalized macrocyclic core of iriomoteolide 3a, a cytotoxic 15-membered macrolide, is disclosed. The key steps involve Sharpless asymmetric dihydroxylation, Sharpless asymmetric epoxidation, olefin cross-metathesis, Yamaguchi esterification, and a ring-closing metathesis reaction for macrocyclization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Dinoflagellida / chemistry
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure

Substances

Iriomoteolide-3a
Macrolides