| Autor: |
O'Connor PD; Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210-1185, USA., Knight CK, Friedrich D, Peng X, Paquette LA |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2007 Mar 02; Vol. 72 (5), pp. 1747-54. Date of Electronic Publication: 2007 Feb 02. |
| DOI: |
10.1021/jo062513f |
| Abstrakt: |
Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed 1H and 13C NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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