Sharpe Robert J, Johnson Jeffrey S
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
J Am Chem Soc. 2015 Apr 22;137(15):4968-71. doi: 10.1021/jacs.5b02631. Epub 2015 Apr 9.
A stereocontrolled total synthesis of the indole diterpenoid natural product paspaline is described. Key steps include a highly diastereoselective enzymatic desymmetrization, substrate-directed epoxidation, Ireland-Claisen rearrangement, and diastereotopic group selective C-H acetoxylation to assemble the target with excellent stereofidelity. The route and results described herein outline complementary conceptual disconnections in the arena of steroid natural product synthesis.
本文描述了吲哚二萜类天然产物巴斯帕灵的立体控制全合成。关键步骤包括高度非对映选择性的酶促去对称化、底物导向的环氧化、爱尔兰-克莱森重排以及非对映异位基团选择性的C-H乙酰氧基化，以优异的立体保真度构建目标产物。本文所述的路线和结果概述了甾体天然产物合成领域中互补的概念性切断。
