Tetrahedron: Asymmetry

An efficient synthesis of enantiopure SDZ 267–489 via a resolution/racemization method

…, PG Mattner, A Kucerovy, K Prasad, O Repic

Index: Xu, Daqiang; Mattner, Paul G.; Kucerovy, Andrew; Prasad, Kapa; Repic, Oljan Tetrahedron Asymmetry, 1996 , vol. 7, # 3 p. 747 - 754

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Citation Number: 5

Abstract

A new synthesis of (R)-3-methyl-5-phenyl-5H-thiazolo [2, 3-b] quinazoline 1, a serum HDL cholesterol raising agent, is described utilizing a resolution of the racemic compound with D- tartaric acid. The undesired S-enantiomer was recycled using either a photochemical or thermal electrocyclic ring opening/closing reaction making the synthesis economical.