Université de Lyon - Université Claude Bernard Lyon 1 - CNRS - INSA Lyon - CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires - UMR 5246, équipe SURCOOF, Campus Lyon-Tech-La Doua, bât. Raulin, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France.
Org Biomol Chem. 2020 Mar 11;18(10):1949-1956. doi: 10.1039/c9ob02639h.
A new and straightforward synthesis of the C1-C7 core fragment of nhatrangin A was achieved in 14 steps from achiral 3-hydroxybenzaldehyde, without the need of chiral reagents or enzymatic resolution to introduce the chiral centers. The key asymmetric steps include in particular a highly enantioselective organocatalyzed Michael addition on an aryl vinyl ketone, a Sharpless asymmetric epoxidation and a subsequent regioselective ring opening of the resulting chiral epoxide. This work represents the first formal enantioselective synthesis of nhatrangin A.
一种新型、简洁的从非手性 3-羟基苯甲醛出发，经 14 步反应合成 nhatrangin A 的 C1-C7 核心片段的方法，该方法无需使用手性试剂或酶拆分来引入手性中心。关键的不对称步骤包括：在芳基乙烯酮上进行高度对映选择性的有机催化迈克尔加成、Sharpless 不对称环氧化反应以及随后立体选择性地开环得到的手性环氧化物。这项工作代表了 nhatrangin A 的首次正式对映选择性合成。
