Synthesis of C13-C22 of amphidinolide T2 via nickel-catalyzed reductive coupling of an alkyne and a terminal epoxide |
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Authors: | Karen C. O'Brien |
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Affiliation: | Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA |
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Abstract: | Several stereoselective routes to the synthesis of (1S,3R)-t-butyldimethyl-(1-methyl-3-oxiranyl-propoxy)-silane (13a) were explored, and the use of Jacobsen's hydrolytic kinetic resolution to separate a mixture of diastereomeric epoxides was a key step in the shortest of these. As part of an approach to the total synthesis of amphidinolide T2 (2), this epoxide, corresponding to C17-C22 of the natural product, was successfully joined with an alkyne (C13-C16) by way of a nickel-catalyzed reductive coupling reaction. |
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Keywords: | Nickel Epoxide Alkyne Amphidinolide |
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