Synthesis of the Purported ent-Pochonin J Structure Featuring a Stereoselective Oxocarbenium Allylation

D Martinez-Solorio, KA Belmore…

Index: Martinez-Solorio, Dionicio; Belmore, Kenneth A.; Jennings, Michael P. Journal of Organic Chemistry, 2011 , vol. 76, # 10 p. 3898 - 3908

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Citation Number: 20

Abstract

The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti- reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the α-C-glycoside subunit is highlighted by a mismatched oxocarbenium ...