Enantioselective synthesis of (3R, 4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum
J Garcia, M López, J Romeu
Index: Garcia, Jordi; Lopez, Marta; Romeu, Joan Tetrahedron Asymmetry, 1999 , vol. 10, # 13 p. 2617 - 2626
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Citation Number: 27
Abstract
The first stereoselective synthesis of (3R, 4E)-19-methylicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1- trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine.
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