Diastereoselective synthesis of dihydropyrans via Prins cyclization of enol ethers: total asymmetric synthesis of (+)-civet cat compound

Sabera Sultana; Kiran Indukuri; Manash J Deka; Anil K Saikia

doi:10.1021/jo4015547

Diastereoselective synthesis of dihydropyrans via Prins cyclization of enol ethers: total asymmetric synthesis of (+)-civet cat compound

J Org Chem. 2013 Dec 6;78(23):12182-8. doi: 10.1021/jo4015547. Epub 2013 Nov 20.

Authors

Sabera Sultana¹, Kiran Indukuri, Manash J Deka, Anil K Saikia

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.

PMID: 24245586
DOI: 10.1021/jo4015547

Abstract

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) can be efficiently used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2H-pyran-2-acetates stereo- and regioselectively in good yields. The methodology was used for the total synthesis of natural product (+)-civet.

Publication types

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

MeSH terms

Animals
Biological Products / chemical synthesis*
Biological Products / chemistry
Cyclization
Ethers / chemistry*
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Stereoisomerism
Viverridae

Substances

Biological Products
Ethers
Pyrans