DOUBLY STEREODIFFERENTIATING HIYAMA ADDITION WITH MISMATCHED REACTANTS - ENANTIOCONTROLLED AND DIASTEREOCONTROLLED SYNTHESIS OF DIHYDROCANADENSOLIDE

Carbon skeleton, functionalization pattern, and chirality centers of the target molecule are formed at once in the key step of the synthesis of 1, a metabolite of Penicillium canadense. This key step is the highly steroselective Hiyama reaction of a chiral allyl bromide derivative with an α‐chiral aldehyde in the mismatched combination with predominance of the allyl components. (Figure Presented.) Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany