Organic letters

Catalytic asymmetric synthesis of phthioceranic acid, a heptamethyl-branched acid from Mycobacterium tuberculosis

B ter Horst, BL Feringa, AJ Minnaard

Index: Ter Horst, Bjorn; Feringa, Ben L.; Minnaard, Adriaan J. Chemical Communications, 2007 , # 5 p. 489 - 491

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Citation Number: 59

Abstract

The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1, 4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1, 3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty ...