Improved synthesis of isogranulatimide, a G2 checkpoint inhibitor. Syntheses Of didemnimide C, isodidemnimide A, neodidemnimide A, 17-methylgranulatimide, and isogranulatimides A-C.
A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.
Piers
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Departments of Chemistry and Earth and Ocean Sciences, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.
Britton
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Andersen
R J
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D016195:G2 Phase / Q000187:drug effects*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D007093:Imidazoles; D007211:Indoles; C116644:isogranulatimide