Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5222057 | Tetrahedron | 2011 | 15 Pages |
Abstract
Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in SEâ² reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at â78 °C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of SEâ² reactions leading to the C1-C9 aldehyde 14, and the bis-tetrahydropyran 59, respectively.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
David R. Williams, Scott V. Plummer, Samarjit Patnaik,