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Paper | Regular issue | Vol 51, No. 7, 1999, pp.1527-1541
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8456
The Formal Synthesis of Chiral Etodolac Using Chiral 1,2-Di(alkylcarbonyl)oxypentan-3-one as Chiral Building Block

Shan-Yen Chou,* Chin-Lu Tseng, and Shyh-Fong Chen

*Deparatment of Medicinal Chemistry, Development Center for Biotechnology, Hsi-Chih Research Park 101, Lane 169, Kang Ning St, Hsi Chih 221, Taipei Hsien, Taiwan, R.O.C.

Abstract

A stereoselective synthesis of (+)- and (–)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanols (31) and (32), the key intermediates for chiral etodolac was executed in seven steps starting from the asymmetric cyclization of (2R)-1,2-di(acetyloxypentan)-3-one (5) or (2R)-1,2-di(propionyloxypentan)-3-one (6) and 7-ethyltryptophol (7). Some unexpected transformations are also described.