Highly Stereocontrolled Total Synthesis of β-d-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis

…, L Scharf, EJ Adams, JA Piccirilli

Index: Li, Nan-Sheng; Scharf, Louise; Adams, Erin J.; Piccirilli, Joseph A. Journal of Organic Chemistry, 2013 , vol. 78, # 12 p. 5970 - 5986

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Citation Number: 8

Abstract

β-d-Mannosyl phosphomycoketide (C 32-MPM), a naturally occurring glycolipid found in the cell walls of Mycobacterium tuberculosis, acts as a potent antigen to activate T-cells upon presentation by CD1c protein. The lipid portion of C 32-MPM contains a C 32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with ...