Suchergebnisse

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. ; We thank the Research School of Chemistry, the Australian Research Council and Institute of Advanced Studies for support. JNB is the grateful recipient of an Australian Postgraduate Award (APA) provided by the Australian Government.

A total synthesis of compound 3 from D-(−)-tartaric acid is reported, thereby establishing that the structure, including relative stereochemistry, originally assigned to the cyclic carbonate-containing natural product aspergillusol B is correct. ; We thank the Australian Research Council and the Institute of Advanced Studies for financial support. J.N.B. is the grateful recipient of an APA Scholarship provided by the Australian Government.