Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A

K E Drouet; T Ling; H V Tran; E A Theodorakis

doi:10.1021/ol991290v

Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A

Org Lett. 2000 Jan 27;2(2):207-10. doi: 10.1021/ol991290v.

Authors

K E Drouet¹, T Ling, H V Tran, E A Theodorakis

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0358, USA.

PMID: 10814283
DOI: 10.1021/ol991290v

Abstract

[structure: see text] Reveromycin A (1) belongs to a family of microbial polyketides with unusual structural features and biological activities. The structure of 1 is composed of a [6,6] spiroketal core decorated with highly unsaturated side chains. As a prelude to the synthesis of 1, we present herein a short, efficient, and enantioselective synthesis of the C9-C21 fragment 5 (spiroketal core) of reveromycin A.

Publication types

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

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Epidermal Growth Factor / antagonists & inhibitors
Nuclear Magnetic Resonance, Biomolecular
Protein Synthesis Inhibitors / chemical synthesis
Protein Synthesis Inhibitors / chemistry
Pyrans / chemical synthesis
Pyrans / chemistry*
Spiro Compounds / chemical synthesis
Spiro Compounds / chemistry*
Stereoisomerism
Streptomyces / chemistry

Substances

Antineoplastic Agents
Protein Synthesis Inhibitors
Pyrans
Spiro Compounds
reveromycin A
Epidermal Growth Factor