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Synthesis of an esperamicin core analog with an epoxide trigger

โœ Scribed by Harold Mastalerz; Terrence W Doyle; John F Kadow; Dolatrai M Vyas

Book ID
104255806
Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
198 KB
Volume
37
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An esperamicin core analog 4 with an epoxide trigger like that found in the related enediyne, dynemicin, was prepared. Surprisingly, it was found to be relatively stable; the p-aminophenyl substituent did not facilitate epoxide solvolysis to the extent that had been anticipated. A mild acid, pyridinium p-toluenesulfonate, was found to induce solvolysis of 4 and led to the formation of the cycloaromatized product 25.

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