Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric …
L He, HS Byun, R Bittman
Index: He, Linli; Byun, Hoe-Sup; Bittman, Robert Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7627 - 7633
Full Text: HTML
Citation Number: 49
Abstract
A novel and efficient synthetic route to ceramide 1a and skeleton backbone modified ceramide analogues 1b, c is reported. The syntheses utilize osmium-catalyzed asymmetric dihydroxylation of (E)-α, β-unsaturated ester 5a-c as the chiral induction step, with the desired configurations in the products 1a-c, 2a, and 13 being generated by regioselective azide substitution at the α position of α, β-dihydroxyesters 6a-c via a cyclic ...
Related Articles:
[Mettu, Ravinder; Thatikonda, Narendar Reddy; Olusegun, Oladoye Sunday; Vishvakarma, Ramesh; Vaidya, Jayathirtha Rao Arkivoc, 2012 , vol. 2012, # 6 p. 421 - 436]
A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach
[Torssell, Staffan; Somfai, Peter Organic and Biomolecular Chemistry, 2004 , vol. 2, # 11 p. 1643 - 1646]
A stereoselective synthesis of sphingosine, a protein kinase C inhibitor.
[Nimkar; Menaldino; Merrill; Liotta Tetrahedron Letters, 1988 , vol. 29, # 25 p. 3037 - 3040]
[Lu, Xuequan; Bittman, Robert Tetrahedron Letters, 2005 , vol. 46, # 11 p. 1873 - 1875]
[Boutin, Raymond H.; Rapoport, Henry Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5320 - 5327]