A C1-C9 fragment of the antitumour macrolide rhizoxin has been synthesised. An Evans' asymmetric aldol reaction was used to set up the first two chiral centres, and an a,b-unsaturated d-lactone was then formed on the acyclic system by an intramolecular Wadsworth-Emmons reaction. Stereoselective hydr
Stereocontrolled osmylation of medium-ring alkenes: synthesis of a C1-C9 erythronolide fragment
โ Scribed by Vedejs, E.; Dolphin, J. M.; Mastalerz, H.
- Book ID
- 126144817
- Publisher
- American Chemical Society
- Year
- 1983
- Tongue
- English
- Weight
- 441 KB
- Volume
- 105
- Category
- Article
- ISSN
- 0002-7863
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๐ SIMILAR VOLUMES
The key synthons 2 and 3 [with suitable protecting groups] of the erythronolide A seco acid (1) have been prepared in an enantiomerically pure form, utilizing a stereoselective osmylation of chiral hydroxy (Z,E)-diene ester 6a and subsequent hydrogenation. Recent interest in macrolide and ionophore
An enantioselective route to the C(1) -C(6) erythronolide unit 10 is described, involving the dioxanone-to-dihydropyran enolate Claisen rearrangement (7 + 8), regio-and stereoselective hydroboration to give 9a, and reductive fragmentation of the heterocyclic template (9c + 10). The stereocontrolled