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Paper | Special issue | Vol 95, No. 1, 2017, pp.290-303
Published online, 11th October, 2016
DOI: 10.3987/COM-16-S(S)18
The Synthesis of Polyfunctionalized, Cyclohexene-Based Chirons from Tartaric Acid

Joshua N. Buckler, Brett D. Schwartz, and Martin G. Banwell*

*Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia


Compound ent-1 as well as certain related homochiral and polyfunctionalized cyclohexenes have been prepared from the 1,2-diacetal 4 that is itself readily derived from L-tartaric acid (3). Grignard addition and ring-closing metathesis processes constitute the key steps associated with the reaction sequences involved. This work provides a method for obtaining a range of potentially useful cyclohexenone-containing chirons that are enantiomerically related to those that have been prepared from the homochiral cis-1,2-dihydrocatechol 2, the product of the microbial biotransformation of bromobenzene.