Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University , Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
Org Lett. 2013 Jun 21;15(12):3002-5. doi: 10.1021/ol401214f. Epub 2013 Jun 3.
A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.
已通过 10 步序列，从一种已知的乙烯基酮硅基 N,O-缩醛以 35%的总产率简洁地合成了乳酰咪唑霉素的一个中间体，该中间体是由放线菌产生的含戊二酰亚胺的大环聚酮。这 10 步序列包括两种类型的不对称羟醛缩合反应，以构建所有的立体中心，Stille 偶联反应构建整个碳骨架，以及 Yamaguchi 内酯化反应构建 12 元大环内酯环。
