Convergent total synthesis of bryostatin 8 has been accomplished by an organosilane-based strategy. The C ring is constructed stereoselectively through a geminal bis(silane)-based [1,5]-Brook rearrangement, and the B ring through geminal bis(silane)-based Prins cyclization, thus efficiently joining the northern and southern parts of the molecule.
Enantioselective synthesis of SiMe/SiPhMe-substituted crotyl geminal bis(silane) has been developed. This compound is a useful reagent for PhCB(CF)-catalyzed asymmetric Sakurai allylation and one-pot Sakurai allylation/Prins cyclization processes. Chemoselective desilylation of SiPhMe leads to efficient chirality transfer.
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