通过催化不对称分子内环丙化反应，α-重氮-β-酮二苯膦氧化物，对映选择性全合成（+）-colletoic 酸。
Enantioselective total synthesis of (+)-colletoic acid via catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide.
机构信息
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
出版信息
Org Lett. 2013 Mar 1;15(5):1004-7. doi: 10.1021/ol303459x. Epub 2013 Feb 11.
The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).
本文描述了（+）-colletoic 酸的对映选择性全合成，（+）-colletoic 酸是一种强效的天然存在的 11β-羟甾脱氢酶 1（11β-HSD1）抑制剂。该全合成的特点是α-重氮-β-酮二苯膦氧化物的高对映选择性催化不对称分子内环丙烷化以及五个高度立体选择性的反应（环丙烷开环、Diels-Alder 反应、碘内酯化、烯烃形成和α，β-不饱和羧酸的还原）。
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