Concise synthesis of the oxapentacyclic core of cortistatin A

Fangmiao Yu; Guozhi Li; Peng Gao; Hongju Gong; Yinghua Liu; Yongming Wu; Bin Cheng; Hongbin Zhai

doi:10.1021/ol102058f

Concise synthesis of the oxapentacyclic core of cortistatin A

Org Lett. 2010 Nov 19;12(22):5135-7. doi: 10.1021/ol102058f. Epub 2010 Oct 6.

Authors

Fangmiao Yu¹, Guozhi Li, Peng Gao, Hongju Gong, Yinghua Liu, Yongming Wu, Bin Cheng, Hongbin Zhai

Affiliation

¹ The Key Laboratory of Synthetic Chemistry of Natural Substances and the State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 20925326
DOI: 10.1021/ol102058f

Abstract

A concise synthetic approach for constructing the oxapentacyclic framework of cortistatin A is described. The synthesis features a furan-oxyallyl [4 + 3] cycloaddition and double-intramolecular aldol reactions. In addition, an interesting core structure was obtained in 11 steps from furan by using our method.

Publication types

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

MeSH terms

Animals
Cyclization
Marine Biology
Molecular Structure
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry
Porifera / chemistry
Stereoisomerism

Substances

Polycyclic Compounds
cortistatin A