81678-44-6Relevant articles and documents
Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes
Shoba, Veronika M.,Takacs, James M.
supporting information, p. 5740 - 5743 (2017/05/04)
Oxime-directed catalytic asymmetric hydroboration is diverted to catalytic asymmetric hydrogenation (CAH) upon the addition of a proton source, such as MeOH, or by running the reaction under a hydrogen atmosphere. A borane (e.g., pinacolborane) is require
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.
Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters
Munoz, Lourdes,Bosch, Ma Pilar,Rosell, Gloria,Guerrero, Angel
experimental part, p. 420 - 424 (2009/09/06)
The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on