Synthesis of (±)-Hamigeran B, (−)-Hamigeran B, and (±)-1-epi-Hamigeran B:  Use of Bulky Silyl Groups to Protect a Benzylic Carbon−Oxygen Bond from Hydrogenolysis

2004-04-16T00:00:00Z (GMT) by Derrick L. J. Clive Jian Wang
Enone 42 was converted into diene 56, which was then subjected to hydrogenation. Use of the tert-butyldimethylsiloxy groups enforces facial selectivity and protects the C(5) oxygen from hydrogenolysis. The resulting product (55) is easily converted into hamigeran B (1), a marine natural product with powerful activity against herpes and polio viruses. Optically pure enone 73 was made by use of a Meyers' auxiliary and converted into (−)-hamigeran B with the natural absolute configuration.