Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach

Adele E Pasqua; Frank D Ferrari; Chris Hamman; Yanzhou Liu; James J Crawford; Rodolfo Marquez

doi:10.1021/jo301210f

Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach

J Org Chem. 2012 Aug 17;77(16):6989-97. doi: 10.1021/jo301210f. Epub 2012 Aug 2.

Authors

Adele E Pasqua¹, Frank D Ferrari, Chris Hamman, Yanzhou Liu, James J Crawford, Rodolfo Marquez

Affiliation

¹ School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.

PMID: 22804781
DOI: 10.1021/jo301210f

Abstract

The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.

Publication types

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

MeSH terms

Alkenes / chemical synthesis*
Amides / chemical synthesis*
Antifungal Agents / chemical synthesis*
Boron Compounds / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Alkenes
Amides
Antifungal Agents
Boron Compounds
crocacin C