A practical approach to the asymmetric synthesis of the ring A substructure of genkwadane A, a daphnane diterpenoid, was developed. This synthesis features the Mukaiyama aldol reaction to introduce the quaternary ster...A practical approach to the asymmetric synthesis of the ring A substructure of genkwadane A, a daphnane diterpenoid, was developed. This synthesis features the Mukaiyama aldol reaction to introduce the quaternary stereogenic center at C4 and VO(acac)2-catalyzed Jackson-Ellman-Bolrn sulfoxidation to deliver the corresponding sulfoxide. The Dieckmann-type condensation was efficiently promoted by KHMDS and the ring A substructure was finally accomplished through Barton iodination condition.展开更多
文摘A practical approach to the asymmetric synthesis of the ring A substructure of genkwadane A, a daphnane diterpenoid, was developed. This synthesis features the Mukaiyama aldol reaction to introduce the quaternary stereogenic center at C4 and VO(acac)2-catalyzed Jackson-Ellman-Bolrn sulfoxidation to deliver the corresponding sulfoxide. The Dieckmann-type condensation was efficiently promoted by KHMDS and the ring A substructure was finally accomplished through Barton iodination condition.