The first synthesis of a 12-membered macrolide natural product via a RCM protocol: determination of absolute stereochemistry
PR Krishna, R Srinivas
Index: Krishna, Palakodety Radha; Srinivas, Ravula Tetrahedron Asymmetry, 2008 , vol. 19, # 9 p. 1153 - 1160
Full Text: HTML
Citation Number: 9
Abstract
The first synthesis of (10S, 12R)-10-hydroxy-12-methyl-1-oxacyclododecane-2, 5-dione and its C12 epimer is reported, thereby assigning the absolute stereochemistry of the natural product. The strategy utilizes a syn selective reduction, Yamaguchi esterification, and ring- closing metathesis as the key steps.
Related Articles:
Bifunctional inhibitors of mevalonate kinase and mevalonate 5-diphosphate decarboxylase
[Organic Letters, , vol. 8, # 6 p. 1013 - 1016]
[Journal of the American Chemical Society, , vol. 109, # 11 p. 3491 - 3493]
Total synthesis of allocyathin B2, a metabolite of bird's nest fungi
[Journal of Organic Chemistry, , vol. 63, # 2 p. 306 - 313]
A stereocontrolled synthesis of dl-biflora-4, 10 (19), 15-triene
[Journal of Organic Chemistry, , vol. 51, # 21 p. 4023 - 4028]