164907-39-5Relevant academic research and scientific papers
Stereoselective formal total synthesis of the cyclodepsipeptide (-)-spongidepsin
Chandrasekhar, Srivari,Yaragorla, Srinivasa Rao,Sreelakshmi, Lella
, p. 7339 - 7342 (2007)
The formal total synthesis of (-)-spongidepsin is achieved starting from easily available raw materials involving asymmetric α-hydroxylation, Enders alkylation, and RCM as key reactions.
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.
Stereoselective synthesis of C1-C9 and C9-C17 fragments of (+)-13-deoxytedanolide
Yadav,Rami Reddy
experimental part, p. 3265 - 3274 (2010/06/15)
An efficient and highly stereoselective asymmetric synthesis of C1-C9 and C9-C17 fragments of (+)-13-deoxytedanolide have been achieved. Utilization of desymmetrization technique to prepare the triol with five stereogenic centers, regioselective Sharpless asymmetric dihydroxylation, Evans' aldol reaction, chiral methylation, and Wittig olefination are highlights of the synthesis.
Formal total synthesis of (-)-spongidepsin
Chandrasekhar,Yaragorla,Sreelakshmi,Reddy, Ch. Raji
, p. 5174 - 5183 (2008/12/20)
The formal total synthesis of (-)-spongidepsin is described. Three fragments I, II, and III were first prepared from readily available starting materials and then assembled to the target compound. The key steps involved in the synthesis are asymmetric α-hydroxylation, Ender's alkylation, and ring-closing metathesis reactions. An alternative route for the fragment II is also achieved involving Sharpless asymmetric epoxidation and Gilman's alkylation as key reactions.
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
Biosynthesis of Tetronasin: Part 4, Preparation of Deuterium Labelled C19-C26, C17-C26, C11-C26 and C3-C26 Polyketide Fragments as Putative Biosynthetic Precursors of the Ionophore Antibiotic Tetronasin (ICI 139603)
Boons, Geert-Jan,Clase, J. Andrew,Lennon, Ian C.,Ley, Steven V.,Staunton, James
, p. 5417 - 5446 (2007/10/02)
Six deuterium labelled N-acylcysteamine polyketide derivatives (3) - (8) have been prepared as putative precursors for incorporation in studies of the biosynthesis of the ionophore antibiotic tetronasin (1).The route to these compounds was designed to be
