Synthesis of the FG Ring System of Brevetoxin B

Article abstract of DOI:10.1021/ja00199a030

A synthesis of an appropriately functionalized system (1) representing the FG ring skeleton of brevetoxin B is described.Beginning with the geraniol-derived lactone 6, the reported sequence proceeds via key intermediates 15 and 27 and involves two 6-endo selective hydroxy epoxide openings leading to the optically active target 1.The stereochemistry of the final product was confirmed by an X-ray crystallographic analysis of the crystalline derivative 30.