Synthesis of the aglycones of altromycins and kidamycin from a common intermediate.
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]
Fei
ZhongBo
Z
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
McDonald
Frank E
FE
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry
D000617:Aminoglycosides; D000903:Antibiotics, Antineoplastic; C100062:kidamycin; C063716:altromycin A