手性选择性合成冠状脂肪酸的所有可能立体异构体。

Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid.

机构信息

Graduate School of Life Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai, 980-8578, Japan.

Graduate School of Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai, 980-8578, Japan.

出版信息

ChemistryOpen. 2020 Oct 9;9(10):1008-1017. doi: 10.1002/open.202000210. eCollection 2020 Oct.

DOI:10.1002/open.202000210

PMID:33072470

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7545439/

Abstract

An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels-Alder type cycloaddition using a chiral auxiliary. CFA and 6--CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6--CFA, we established that its -fused configuration is important for the introduction of C4-C5 double bond by dehydration. This report is the first practical synthesis of both 6--CFA, and its enantiomer.

摘要

已开发出一种高效且对映选择性的 Coronafacic 酸（CFA）所有可能立体异构体的合成方法。通过使用手性辅助剂，在非对映选择性 Diels-Alder 型环加成反应中控制 C3a 和 C7a 的立体化学。CFA 和 6--CFA 通过共同中间体的氢化合成。在 6--CFA 的合成过程中，我们确定其 -稠合构型对于通过脱水引入 C4-C5 双键很重要。本报告首次实用地合成了 6--CFA 及其对映异构体。