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Synthesis of the aglycones of altromycins and kidamycin from a common intermediate.

ABSTRACT: The aglycone structures 1 and 2, respectively corresponding to the antitumor antibiotic natural products altromycin and kidamycin, have been efficiently synthesized from a common advanced intermediate 3. A series of Claisen condensations and aromatizations affords the anthracene section of 3, followed by annulation of the pyrone ring. The functional groups of 3 can be manipulated for enantioselective introduction of the epoxide side-chain of altromycin aglycone 1, as well as synthesis of the kidamycin aglycone 2. [reaction: see text]

SUBMITTER: Fei Z

PROVIDER: S-EPMC1388187 | biostudies-literature | 2005 Aug

REPOSITORIES: biostudies-literature

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Synthesis of the aglycones of altromycins and kidamycin from a common intermediate.

Fei ZhongBo Z McDonald Frank E FE

Organic letters 20050801 17

The aglycone structures 1 and 2, respectively corresponding to the antitumor antibiotic natural products altromycin and kidamycin, have been efficiently synthesized from a common advanced intermediate 3. A series of Claisen condensations and aromatizations affords the anthracene section of 3, followed by annulation of the pyrone ring. The functional groups of 3 can be manipulated for enantioselective introduction of the epoxide side-chain of altromycin aglycone 1, as well as synthesis of the kid ...[more]

PMID: 16092833

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