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Synfacts 2007(4): 0347-0347
DOI: 10.1055/s-2007-968281
DOI: 10.1055/s-2007-968281
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (+)-Acutiphycin
R. M. Moslin, T. F. Jamison*
Massachusetts Institute of Technology, Cambridge, USA
Further Information
Publication History
Publication Date:
23 March 2007 (online)

Significance
(+)-Acutiphycin, isolated from the blue-green alga Oscillatoria acutissma, displays in vivo activity against Lewis lung carcinoma and is cytotoxic toward various cancer cell lines. Noteworthy in this synthesis is (1) the three-stage, one-pot preparation of δ-lactone H, (2) an intermolecular SmI2-mediated Reformatsky reaction and (3) macrolactonization by intramolecular ketene capture.