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Total Synthesis of the Callipeltoside Aglycon
Ian Paterson1, Robert D M Davies1, Rodolfo Marquez1
1University Chemical Laboratory Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336362.
Abstract:
Following macrolactonization, a Sonogashira coupling leads efficiently from 1 and 2 to the aglycon of the structurally unique cytotoxic macrolide callipeltoside A, isolated in tiny quantities from the lithistid sponge Callipelta sp. Key steps in the preparation of macrolide precursor 1 include a boron-mediated anti-aldol coupling (A) in tandem with Yamamoto's vinylogous aldol reaction (B). TES=triethylsilyl.
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