Synthesis of the C(21)−C(26) Fragment of Superstolide A: Concerning the Stereochemistry of (E)-Crotylboration Reactions of Alaninal Derivatives
- 12 April 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (10), 3838-3843
- https://doi.org/10.1021/jo0341012
Abstract
A stereoselective synthesis of the C(21)-C(26) fragment of superstolide A has been completed. The absolute and relative stereochemistry of intermediate 14 has been conclusively proven by NMR and X-ray diffraction methods. In the course of this work, it was found that the stereochemistry of 3 had been misassigned in our previously reported synthesis of the C(18)-C(26) segment. This error stems from the unexpected diastereoselectivity in the double asymmetric reaction of N-acetyl-d-alaninal 1 and the tartrate ester modified (E)-crotylboronate (R,R)-2.Keywords
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