Total synthesis of the marine toxin phorboxazole A using palladium (II)-mediated intramolecular alkoxycarbonylation for tetrahydropyran synthesis

P Kuntiyong, TH Lee, CL Kranemann…

Index: Kuntiyong, Punlop; Lee, Tae Hee; Kranemann, Christian L.; White, James D. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 39 p. 7884 - 7899

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Citation Number: 7

Abstract

The potent antitumor agent phorboxazole A was synthesized from six subunits comprising C1–C2 (115), C3–C8 (98), C9–C19 (74), C20–C32 (52), C33–C41 (84) and C42–C46 (85). Tetrahydropyrans B and C containing cis-2, 6-disubstitution were fabricated via palladium (II)-mediated intramolecular alkoxycarbonylation which, in the case of tetrahydropyran C, was carried out with catalytic palladium (II) and p-benzoquinone as the stoichiometric re- ...

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