Stereoselective ketal-tethered intramolecular diels-alder cycloadditions. An approach to the 2-oxadecalin spiroketal core of antifungal agent fusidilactone C

Jiashi Wang; Richard P Hsung; Sunil K Ghosh

doi:10.1021/ol0495624

Stereoselective ketal-tethered intramolecular diels-alder cycloadditions. An approach to the 2-oxadecalin spiroketal core of antifungal agent fusidilactone C

Org Lett. 2004 Jun 10;6(12):1939-42. doi: 10.1021/ol0495624.

Authors

Jiashi Wang¹, Richard P Hsung, Sunil K Ghosh

Affiliation

¹ Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

PMID: 15176788
DOI: 10.1021/ol0495624

Abstract

[reaction: see text] An approach toward the 2-oxadecalin spiroketal core of fusidilactone C via a rare ketal-tethered intramolecular Diels-Alder cycloaddition is described here. This intramolecular Diels-Alder cycloaddition is highly endo-selective and overall depended upon the nature of solvents and Lewis acids. We also observed some remarkable rate acceleration in MeOH.

Publication types

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

MeSH terms

Antifungal Agents / chemical synthesis*
Cyclization
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Conformation
Naphthalenes / chemical synthesis*
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Antifungal Agents
Lactones
Naphthalenes
Spiro Compounds
fusidilactone A
fusidilactone C
oxadecalin