948859-79-8Relevant academic research and scientific papers
Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica
Geerdink, Danny,Buter, Jeffrey,Van Beek, Teris A.,Minnaard, Adriaan J.
, p. 761 - 766 (2014)
Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)- 4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner-Wadsworth-Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%.
Asymmetric Total Synthesis of Mycobacterial Diacyl Trehaloses Demonstrates a Role for Lipid Structure in Immunogenicity
Holzheimer, Mira,Reijneveld, Josephine F.,Ramnarine, Alexandrea K.,Misiakos, Georgios,Young, David C.,Ishikawa, Eri,Cheng, Tan-Yun,Yamasaki, Sho,Moody, D. Branch,Van Rhijn, Ildiko,Minnaard, Adriaan J.
, p. 1835 - 1841 (2020/08/26)
The first asymmetric total synthesis of three structures proposed for mycobacterial diacyl trehaloses, DAT1, DAT2, and DAT3 is reported. The presence of two of these glycolipids, DAT1 and DAT3, within different strains of pathogenic M. tuberculosis was co
A concise asymmetric synthesis of (-)-rasfonin
Huang, Yange,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 29 - 31 (2012/01/19)
A very efficient total synthesis of the apoptosis inducer (-)-rasfonin has been developed using CuBr/JosiPhos catalyzed iterative asymmetric conjugate addition of MeMgBr and Feringa's butenolide.
Catalytic asymmetric synthesis of mycolipenic and mycolipanolic acid
Horst, Bjorn Ter,Van Wermeskerken, Jeroen,Feringa, Ben L.,Minnaard, Adriaan J.
supporting information; experimental part, p. 38 - 41 (2010/03/24)
The first asymmetric synthesis of mycolipenic acid and mycolipanolic acid by using an improved iterative procedure involving catalytic asymmetric conjugate addition of MeMgBr as the key step is described. Mycolipenic and mycolipanolic acid are obtained in 11 steps with perfect stereocontrol, and both acids are identical to their counterparts from natural sources.
Formal synthesis of the anti-angiogenic polyketide (-)-borrelidin under asymmetric catalytic control
Madduri, Ashoka V. R.,Minnaard, Adriaan J.
supporting information; experimental part, p. 11726 - 11731 (2010/11/18)
Borrelidin (1) is a polyketide that possesses extremely potent antiangiogenesis activity. This paper describes its formal total synthesis by the most efficient route to date. This modular approach takes optimal benefit of asymmetric catalysis and permits the synthesis of analogues; in addition, the high yields and selectivities obtained eliminate the need for separation of stereoisomers. The upper half of borrelidin has been accessed by iterative copper-catalysed asymmetric conjugate addition of methylmagnesium bromide, whereas synthesis of the lower half of the molecule was achieved by relying on asymmetric hydrogenation and cross-methathesis as key steps.
