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The dioxanone-to-dihydropyran Claisen rearrangement. Synthesis of C(7)-C(13) fragments of erythronolides A and B

โœ Scribed by Steven D. Burke; Frank J. Schoenen; Mangalam S. Nair

Book ID
108382784
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
395 KB
Volume
28
Category
Article
ISSN
0040-4039

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๐Ÿ“œ SIMILAR VOLUMES

The ester enolate claisen rearrangement.
The ester enolate claisen rearrangement. Synthesis of A C(1)๎—ธC(6) erythronolide fragment
โœ Steven D. Burke; Frank J. Schoenen; Charles W. Murtiashaw ๐Ÿ“‚ Article ๐Ÿ“… 1986 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 319 KB

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