Synthesis of an Acyclic C1–C11 Fragment of Peloruside B

Q Zang, S Gulab, BL Stocker, S Baars…

Index: Zang, Qin; Gulab, Shivali; Stocker, Bridget L.; Baars, Sylvia; Hoberg, John O. European Journal of Organic Chemistry, 2011 , # 23 p. 4465 - 4471

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Citation Number: 2

Abstract

Abstract The synthesis of a C1 reduced form of the C1–C11 fragment of peloruside B has been achieved in 15 synthetic steps. The strategy involved the use of D-tartaric acid to set the absolute stereochemistry and a 1, 5-anti Mukiayama aldol reaction. Analog synthesis of C8–C11 is also reported, which enables changes at the C10 position of peloruside B to be made. The synthesis of the fragment concludes with C1 in the protected alcohol state ...