Six-Step Synthesis of Alcyopterosin A, a Bioactive Illudalane Sesquiterpene with a gem-Dimethylcyclopentane Ring

Tung T Hoang; Mélodie Birepinte; Nicholas J Kramer; Gregory B Dudley

doi:10.1021/acs.orglett.6b01665

Six-Step Synthesis of Alcyopterosin A, a Bioactive Illudalane Sesquiterpene with a gem-Dimethylcyclopentane Ring

Org Lett. 2016 Jul 15;18(14):3470-3. doi: 10.1021/acs.orglett.6b01665. Epub 2016 Jun 30.

Authors

Tung T Hoang¹, Mélodie Birepinte¹, Nicholas J Kramer¹, Gregory B Dudley¹

Affiliation

¹ Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306-4390, United States.

PMID: 27359158
DOI: 10.1021/acs.orglett.6b01665

Abstract

Strategic pairing of ring openings and cycloisomerization provides rapid and efficient "open and shut" entry into sparsely functionalized illudalanes, as exemplified here in the context of a six-step synthesis of alcyopterosin A. Key steps include a tandem ring-opening fragmentation/olefination process for preparing a neopentyl-tethered 1,6-enyne, ring-opening olefination telescoped with alkyne homologation, and Rh-catalyzed oxidative cycloisomerization.

Publication types

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