872530-62-6Relevant articles and documents
Highly stereocontrolled total synthesis of β-d-mannosyl phosphomycoketide: A natural product from mycobacterium tuberculosis
Li, Nan-Sheng,Scharf, Louise,Adams, Erin J.,Piccirilli, Joseph A.
, p. 5970 - 5986 (2013/07/26)
β-d-Mannosyl phosphomycoketide (C32-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 C32-MPM contains a C32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with high stereopurity (>96%) using Julia-Kocienski olefinations followed by diimide reduction. By careful choice of olefination sites, we could derive all chirality from a single commercial compound, methyl (2S)-3-hydroxy-2-methylpropionate (>99% ee). Our approach is the first highly stereocontrolled method to prepare C32-MPM molecule with >96% stereopurity from a single >99% ee starting material. We anticipate that our methods will facilitate the highly stereocontrolled synthesis of a variety of other natural products containing chiral oligoisoprenoid-like chains, including vitamins, phytol, insect pheromones, and archaeal lipids.
Total synthesis of halipeptins: Isolation of halipeptin D and synthesis of oxazoline halipeptin analogues
Nicolaou,Schlawe, Daniel,Kim, David W.,Longbottom, Deborah A.,De Noronha, Rita G.,Lizos, Dimitrios E.,Manam, Rama Rao,Faulkner, D. John
, p. 6197 - 6211 (2007/10/03)
The isolation from the marine sponge Leiosella cf. arenifibrosa and structural elucidation of halipeptin D (5). a relative of the previously isolated halipeptins A-C (1-3), is described along with the total synthesis of a number of oxazoline analogues (7a
