270064-35-2Relevant academic research and scientific papers
Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran
Nesbitt, Caroline L.,McErlean, Christopher S. P.
experimental part, p. 2198 - 2208 (2011/05/04)
The total synthesis of the C19 lipid diols 5 and 6, the enantiomers of the anthelmintic marine natural products 1 and 3, is described. Key steps in the divergent syntheses include a syn selective epoxidation of a homoallylic alcohol, a one-pot alkoxypalladation-carbonylation-lactonisation reaction sequence and a DMEAD promoted Mitsunobu inversion.
An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans
Nesbitt, Caroline L.,McErlean, Christopher S.P.
supporting information; experimental part, p. 6318 - 6320 (2010/01/18)
Single enantiomer 2,5-disubstituted-3-oxygenated tetrahydrofurans are synthesized in as little as four steps from a commercially available epoxide. The key steps are homoallylic alcohol epoxidation, palladium-catalysed alkoxy-carbonylation-lactonisation and Mitsunobu inversion. The protocol is applied to the formal total syntheses of (+)-kumausallene, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol and the core of lytophilippine A.
A general strategy for the formal synthesis of (-)-trans-kumausyne and total synthesis of (5R)-Hagen's gland lactones from diacetone-D-glucose
Mereyala, Hari Babu,Gadikota, Rajendrakumar Reddy
, p. 743 - 751 (2007/10/03)
A general strategy for the formal synthesis of (-)-trans-kumausyne 1 via the bicyclic lactone (3aR,5R,6aR)-4 and total synthesis of (5R)-Hagen's gland lactones 2 and 3 via bicyclic lactone (3aR,5S,6aR)-5 starting from diacetone-D-glucose 6 is described. Syntheses of 4 and 5 were achieved by Wittig olefination-lactonization-Michael addition of the corresponding lactols 16 and 17, respectively. Copyright (C) 2000 Elsevier Science Ltd.
