Publication

Asymmetric Total Synthesis of (11r,12s,13s,9z,15z)-9,12,13-Trihydroxyoctadeca-9,15-Dienoic Acid, a Self-Defensive Agent against Rice-Blast Disease

Pierre Vogel
1994
Journal Articles

Abstract

The Diels-Alder adduct of furan and 1-cyanovinyl (1'R)-camphanate was converted into methyl[(tert-butyl)dimethylsilyl 5-deoxy-2,3-O-isopropylidene-beta-L-ribo-hexofuranosid]uronate ((+)-4). Reduction with diisobutylaluminium hydride gave the corresponding aldehyde which was condensed with the ylide derived from triphenyl(propyl)phosphonium bromide to give (1R,2S,3S,4S)-1-[(tert-butyl)dimethylsilyloxy]tetrahydro-2,3-(isopropyli denedioxy)-4-[(Z)-pent-2'-enyl]furan ((+)-7). Removal of the silyl protective group gave a mixture of the corresponding furanose that underwent Wittig reaction with the ylide derived from [8-(methoxycarbonyl)octyl]triphenylphosphonium bromide to yield methyl (11R,12S,13S,9Z,15Z)-13-hydroxy-11,12-(isopropylidenedioxy)octadeca-9,15 -dienoate ((-)-9). Acidic hydrolysis, then saponification afforded (11R,12S,13S,9Z,15Z)-11,12,13-trihydroxyoctadeca-9, 15-dienoic acid (1).

Official source

https://infoscience.epfl.ch/entities/publication/59960f1a-e2b8-4a8a-9f87-2e50dd0dfddf

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Pierre Vogel
1994
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/59960f1a-e2b8-4a8a-9f87-2e50dd0dfddf

About this result

Related concepts (7)

Rice

Rice is the seed of the grass species Oryza sativa (Asian rice) or, less commonly, O. glaberrima (African rice). The name wild rice is usually used for species of the genera Zizania and Porteresia, both wild and domesticated, although the term may also be used for primitive or uncultivated varieties of Oryza. As a cereal grain, domesticated rice is the most widely consumed staple food for over half of the world's human population, particularly in Asia and Africa.

Upland rice

Upland rice is a type of rice grown on dry soil rather than flooded rice paddies. It is sometimes also called dry rice. Today nearly 100 million people depend on upland rice as their daily staple food. Almost two-thirds of the upland rice area is in Asia, with Bangladesh, Cambodia, China, Northeastern India, Indonesia, Myanmar, Nepal, Thailand and Vietnam being important producers. Upland rice is grown in rainfed fields prepared and seeded when dry, much like wheat or maize.

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.