School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Org Biomol Chem. 2018 Apr 25;16(16):3018-3025. doi: 10.1039/c8ob00603b.
A divergent strategy has been used for the concise and efficient enantioselective formal synthesis of Annonaceous acetogenin cis-solamin. Our synthetic strategy comprises concise preparation of the diepoxyester via an 11-membered silaketal constructed by ring-closing metathesis after the dimerization of chiral epoxides, and uses an acid-catalyzed tandem intramolecular SN2-like reaction to construct the threo-cis-threo configuration of the tetrahydrofuran-diol moiety.
我们采用了一种发散性策略，以简洁高效的方式对 Annonaceous acetogenin cis-solamin 进行对映选择性的形式合成。我们的合成策略包括通过手性环氧化物二聚化后形成的 11 元硅缩酮进行环 closing metathesis 制备简洁的双环氧酯，以及利用酸催化的串联分子内 SN2 样反应构建四氢呋喃二醇部分的 threo-cis-threo 构型。
