THE SYNTHESIS OF (+)-PERICOSINE-B

The first synthesis of (+)-pericosine B is described: this takes seven steps and proceeds in 10% overall yield. The key step in our work is a hydrogen-bonding controlled contra-steric dihydroxylation reaction u sing osmium tetroxide and an amine promoter. The absolute stereochemis try of the natural product was deduced from the known absolute stereoc hemistry of our starting material and moreover, the relative and absol ute stereochemistry of our synthetic material was determined unambiguo usly from an X-ray crystal structure of an advanced intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.