Divergent synthesis of lamellarin α 13-sulfate, 20-sulfate, and 13, 20-disulfate

M Iwao, T Fukuda, S Saeki, T Ohta

Index: Fukuda, Tsutomu; Ohta, Takeshi; Saeki, Sho; Iwao, Masatomo Heterocycles, 2010 , vol. 80, # 2 p. 841 - 846

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Citation Number: 13

Abstract

A divergent synthesis of three sulfate derivatives of lamellarin α, namely, lamellarin α 13- sulfate (2), 20-sulfate (1), and 13, 20-disulfate (4) has been achieved via a common intermediate (6) in which 13-OH and 20-OH of the lamellarin core are differentially protected by MOM and benzyl groups, respectively. Compound (6) in turn was prepared using sequential Suzuki-Miyaura coupling of 3, 4-dihydroxypyrrole bistriflate (7) as a key ...