经最长线性序列的七步反应合成氯化磺脂 mytilipin A。
A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.
机构信息
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA 92697-2025 (USA) http://www.chem.uci.edu/∼cdv.
出版信息
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):10052-5. doi: 10.1002/anie.201304565. Epub 2013 Aug 8.
Abstract
Magnificent seven: The chlorosulfolipid mytilipin A was synthesized in racemic form in seven steps and in enantioenriched form in eight steps. Key transformations include a highly diastereoselective bromoallylation of a sensitive α,β-dichloroaldehyde, a kinetic resolution of a vinyl epoxide, a convergent and highly Z-selective alkene cross-metathesis, and a chemoselective and diastereoselective dichlorination of a complex diene.
摘要
壮丽的七步曲
氯磺酸酯肌肽 A 以外消旋形式经七步合成，以对映体富集形式经八步合成。关键转化包括对敏感的 α,β-二氯醛进行高非对映选择性溴烯丙基化、乙烯基环氧化物的动力学拆分、高 Z 选择性烯键交叉复分解的收敛和集中、以及复杂二烯的化学选择性和非对映选择性二氯化。
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