The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin

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Contents Vol 62(9)

doi:10.1071/CH09283

The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin

Alison D. Findlay ^A, Antje Gebert ^A, Ian A. Cade ^A, Martin G. Banwell ^A ^B

^A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
^B Corresponding author. Email: mgb@rsc.anu.edu.au





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Australian Journal of Chemistry 62(9) 1173–1180 http://dx.doi.org/10.1071/CH09283
Submitted: 15 May 2009 Accepted: 11 June 2009 Published online: 17 September 2009

Abstract

A seven-step reaction sequence has been used to convert the enantiomerically pure cis-1,2-dihydrocatechol 10 into the cyclohexenone 17a. A near equivalent sequence involving the same starting material has allowed for the synthesis of the regioisomeric system 17b. Compound 17a is related to the A-ring of ent-viridin (ent-1), the non-natural enantiomer of the furanosteroid viridin (1).