Issue 4, 2010

Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks

Abstract

New and simple protocols are described for the conversion of the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol 7 (X = I) and its 6-methylated derivative into either antipodal form of compounds embodying the tricyclic frameworks of terpenoids 1–6. Key steps include intramolecular Diels–Alder (IMDA) and (in some cases) singlet or triplet-based photochemical processes.

Graphical abstract: Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks

Supplementary files

Additions and corrections

Article information

Article type
Communication
Submitted
19 Oct 2009
Accepted
17 Nov 2009
First published
07 Dec 2009

Org. Biomol. Chem., 2010,8, 751-754

Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks

K. A. B. Austin, J. D. Elsworth, M. G. Banwell and A. C. Willis, Org. Biomol. Chem., 2010, 8, 751 DOI: 10.1039/B921600F

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