We report an efficient and convergent strategy for the total synthesis of UCS1025A and its diastereomer tetra-epi-UCS1025A.Ucs1025A is a representative member of the naturally occurring pyrrolizidinone polyketides,fro...We report an efficient and convergent strategy for the total synthesis of UCS1025A and its diastereomer tetra-epi-UCS1025A.Ucs1025A is a representative member of the naturally occurring pyrrolizidinone polyketides,from which members with potent antibacterial,antifungal,and anticancer activities have been identified.Our approach features a tandem carbonylative Stille cross coupling and Diels-Alder reaction to forge a key C-C bond and build the trans-decalin system.This tandem process utilizes carbon monoxide as a one-carbon linchpin to stitch a vinyl triflate and a vinylstannane together and form the desired enone moiety for the subsequent intramolecular Diels-Alder cyclization.Our synthesis also provides a versatile approach for the synthesis of other related pyrrolizidinone-containing polyketides.展开更多
文摘We report an efficient and convergent strategy for the total synthesis of UCS1025A and its diastereomer tetra-epi-UCS1025A.Ucs1025A is a representative member of the naturally occurring pyrrolizidinone polyketides,from which members with potent antibacterial,antifungal,and anticancer activities have been identified.Our approach features a tandem carbonylative Stille cross coupling and Diels-Alder reaction to forge a key C-C bond and build the trans-decalin system.This tandem process utilizes carbon monoxide as a one-carbon linchpin to stitch a vinyl triflate and a vinylstannane together and form the desired enone moiety for the subsequent intramolecular Diels-Alder cyclization.Our synthesis also provides a versatile approach for the synthesis of other related pyrrolizidinone-containing polyketides.
