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ChemInform Abstract: Synthesis of a Hybrid Analogue of the Esperamicin and Dynemicin Cores.

✍ Scribed by H. MASTALERZ; T. W. DOYLE; J. F. KADOW; D. M. VYAS

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of a Hybrid Analogue of the Esperamicin and Dynemicin

Cores.

-The compound (VI) represents an enediyne analogue hybrid of the core structures of esperamicin and dynemicin. Key step in the sequence is the intramolecular Reissert-type reaction of the anion of the Z-1,3-diyn-2-ene (III) to an N-acyl tetrahydrophenanthridinium intermediate. Alkaline hydrolysis of (VI) provides the parent compound (VII) which is only moderately stable. It rapidly rearranges to the allylic alcohol (VIII) which can be easily cycloaromatized to (IX). -(MASTALERZ, H.; DOYLE, T. W.; KADOW,

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