Asymmetric Total Synthesis of Bufospirostenin A
Min-Jing Cheng, Liping Zhong, Chen‐Chen Gu, Xujiang Zhu, Bo Chen, Junshan Liu, Lei Wang, Wen‐Cai Ye, Chuang‐Chuang Li
Abstract
The first and asymmetric total synthesis of bioactive bufospirostenin A, an unusual spirostanol with rearranged A/B rings, was accomplished. The synthetically challenging [5-7-6-5] tetracyclic ring system, found in bufospirostenin A and some other natural products, was efficiently constructed by the unique intramolecular rhodium-catalyzed Pauson-Khand reaction of an alkoxyallene-yne. The 11 stereocenters in the final product, including the 10 contiguous stereocenters, were installed diastereoselectively.
Topics & Concepts
StereocenterChemistryTotal synthesisIntramolecular forceNatural productRing (chemistry)StereochemistryRhodiumEnantioselective synthesisCatalysisOrganic chemistryMarine Sponges and Natural ProductsSynthetic Organic Chemistry MethodsMicrobial Natural Products and Biosynthesis