Catalytic asymmetric synthesis of phthioceranic acid, a heptamethyl-branched acid from Mycobacterium tuberculosis.
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 acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.
ter Horst
Bjorn
B
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborg 4, 9747AG, Groningen, The Netherlands.
Feringa
Ben L
BL
Minnaard
Adriaan J
AJ
D002384:Catalysis; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry*
D005227:Fatty Acids; C522296:phthioceranic acid