Total Synthesis of Aplysiasecosterols A and B, Two Marine 9,11-Secosteroids

Thetotal synthesis of aplysiasecosterols A and B hasbeen accomplished.Key features of the synthesis include the Suzuki-Miyaura couplingof each AB-ring segment and common D-ring segment. The AB-ring segmentof aplysiasecosterol B was synthesized by Shi asymmetric epoxidationas a key reaction. The common D-ring segment was constructed by stereoselectivehydrogenation and Sharpless asymmetric dihydroxylation as key reactions.This late-stage convergent synthesis, which has rarely been reportedin secosteroid synthesis, can be adapted to many 9,11-secosteroids.

Automated summary

The total synthesis of aplysiasecosterols A and B has been accomplished. Key features of the synthesis include the Suzuki-Miyaura coupling of each AB-ring segment and common D-ring segment. This late-stage convergent synthesis, which has rarely been reported in secosteroid synthesis, can be adapted to many 9,11-secosteroids.