Stereospecific Total Synthesis of the Antiviral Agent Hamigeran B-Use of Large Silyl Groups to Enforce Facial Selectivity and to Suppress Hydrogenolysis

摘要

We report the stereospecific synthesis of hamigeran B (1, Scheme 1), which is an important member of a group of related compounds isolated from a marine sponge. Hamigeran B has been found to have strong in vitro activity against polio and herpes viruses but little cytotoxicity. The compound presents a number of constructional problems, and the significant biological properties enhance the potential value of work on its synthesis. One route to hamigeran B and several congeners has been reported. We aimed to deal only with the synthesis of hamigeran B itself and to do so in a stereospecific manner.