jo030347v_si_003.pdf (1.23 MB)
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
journal contribution
posted on 2004-04-16, 00:00 authored by Derrick L. J. Clive, Jian WangEnone 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.