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Total Synthesis of Aplysiasecosterols A and B, Two Marine 9,11-Secosteroids
Takayuki Ohyoshi1, Hidetada Iizumi1, Shu Hosono1
1Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Abstract:
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. The AB-ring segment of aplysiasecosterol B was synthesized by Shi asymmetric epoxidation as a key reaction. The common D-ring segment was constructed by stereoselective hydrogenation and Sharpless asymmetric dihydroxylation as key reactions. This late-stage convergent synthesis, which has rarely been reported in secosteroid synthesis, can be adapted to many 9,11-secosteroids.
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