化学
联轴节(管道)
全合成
组合化学
立体化学
机械工程
工程类
作者
Jack T. Buntine,Samrat Dasgupta,Keely Dorney,Oscar Rubinstein,Mina Salimimarand,Jonathan M. White,Mark A. Rizzacasa
标识
DOI:10.1021/acs.orglett.3c04268
摘要
The first total synthesis of myxobacteria metabolite icumazole A (1) is reported. Key steps in the route include an organocatalyzed asymmetric self-aldol reaction followed by an acetate aldol reaction to form the stereotriad present in the oxazole moiety, an intramolecular Diels–Alder reaction to form the isochromanone, and an acetylide addition and selective methylation. The final steps involved a high-yielding modified Cadiot–Chodkiewicz coupling and stereoselective reduction to secure the Z,Z-diene and afford 1.
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