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Synthèse totale des acides (+) et (–) nonactique à partir de carbohydrates

Ireland, Robert E. and Vevert, Jean-Paul (1981) Synthèse totale des acides (+) et (–) nonactique à partir de carbohydrates. Canadian Journal of Chemistry, 59 (3). pp. 572-583. ISSN 0008-4042.

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The synthesis of (−) and (+) nonactic acids (2a) and (2b) has been achieved starting from D-mannose (7) and D-gluono-γ-lactone (22) respectively. The key step in the synthesis is the [3,3]-sigmatropic rearrangement of the silylated ketene-acetals IV leading to control of the C-2 configuration of nonactic acid. The ketene-acetals were prepared from aliphatic esters of furanoid-glycals II, which were prepared in ten steps from the carbohydrate precursor. The chiral sites of the glycals arise from the corresponding centres in the starting monosaccharide. This type of ketene-acetal Claisen rearrangement leads to products containing the aldol portion required. At the same time knowledge of the absolute configuration of the chiral carbon atom of nonactic acid allows for the determination of the chair or boat form of the transition state of the [3,3]-sigmatropic rearrangement. [Journal translation]

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Additional Information:© 1981 National Research Council of Canada. Conseil national de recherches du Canada. Reçu le 17 Juin 1980. Les auteurs tiennent à remercier l'United States National Science Foundation pour l'attribution d'une bourse (No CHE 7821066) qui a permis la réalisation de ce travail.
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NSFCHE 7821066
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Official Citation:Synthèse totale des acides (+) et (–) nonactique à partir de carbohydrates Robert E. Ireland, Jean-Paul Vevert Canadian Journal of Chemistry, 1981, 59(3): 572-583, 10.1139/v81-083
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:32555
Deposited By: Ruth Sustaita
Deposited On:18 Jul 2012 20:35
Last Modified:23 Aug 2016 10:14

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