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Expeditious syntheses of methyl 8-epi-nonactate and methyl nonactate

✍ Scribed by Aleksander Warm; Pierre Vogel


Book ID
104219359
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
113 KB
Volume
27
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES


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✍ Barry Lygo; Norval O'Connor πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 244 KB

+Metbyl nonactate (2) and (i)-methyl S-epi-nonactate (3), synthetic precursors to the antibiitic nonactin have been syntbcsised, employing the reaction of substituted epoxides with dianions derived from p-ketoesm as the key carbon-carbon bond-forming step.

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Enantioselectiw routes to (+)-methyl nonactate (2) and (-)-m&y1 8-epi-nonactate (3) are described. The cornerstone of this synrktic strategy is a combination of asymmetric silyl tdtro~re cycloaddition and asymmetric reduction, which provides rhe key syn-1 &ii01 intermediate 4. ## Nonactin (1) is an

A general and stereoselective approach t
✍ GΓ©rard Mandville; Christian Girard; Robert Bloch πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 569 KB

A total synthesis of (+)-methyl nonactate from a chiral synthon obtained by enantioselective enzymatic transesterification is described. This new approach involves stereoselective reactions of aldolisation, reduction and intramolecular Michael addition and appears to be quite general since it could