First total synthesis of the E- and Z-isomers of cytospolide-D

作者：Kamal Ahmed^*; Balakrishna Moku; Reddy Papagari Venkat; Rahim Abdul

来源：Tetrahedron: Asymmetry , 2014, 25(2): 148-155.

DOI：10.1016/j.tetasy.2013.12.004

A simple, convergent, and efficient approach for the total synthesis of the bioactive E- and Z-isomers of cytospolide-D is described. The key features of the synthetic strategy include stereoselective methylation, regioselective epoxide opening, olefin cross-metathesis, and a Yamaguchi protocol reaction for the formation of the E-olefinic geometry of the 10 membered ring; Steglich esterification and ring-closing metathesis reaction for the formation of the 10 membered ring with a Z-olefinic geometry in the skeleton. L-Malic acid was used as a chiral pool starting material for the construction of the olefinic acid fragment while D-mannitol was used as a chiral pool starting material for the building of the olefinic alcohol fragment.

• 出版日期2014-1-31