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. 2005 Aug 18;7(17):3617-20.
doi: 10.1021/ol0509742.

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

ZhongBo Fei  1 , Frank E McDonald
Affiliations

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

ZhongBo Fei et al. Org Lett. .

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]

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Figures

Figure 1
Figure 1
Structures of altromycin and kidamycin antitumor antibiotics.
Scheme 1
Scheme 1
Synthesis of 12.
Scheme 2
Scheme 2
Annulation of Pyrone Ring
Scheme 3
Scheme 3
Synthesis of Altromycin Aglycone (1) from 3
Scheme 4
Scheme 4
Synthesis of Kidamycin Aglycone (2) from 3
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