948859-73-2Relevant academic research and scientific papers
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.
Catalytic asymmetric synthesis of phthioceranic acid, a heptamethyl-branched acid from Mycobacterium tuberculosis
Ter Horst, Bjorn,Feringa, Ben L.,Minnaard, Adriaan J.
, p. 3013 - 3015 (2008/02/10)
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.
