Synthesis of cylindricine C and a formal synthesis of cylindricine A

TJ Donohoe, PM Brian, GC Hargaden, TJC O'Riordan

Index: Donohoe, Timothy J.; Brian, Ptoton M.; Hargaden, Grainne C.; O'Riordan, Timothy J.C. Tetrahedron, 2010 , vol. 66, # 33 p. 6411 - 6420

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Citation Number: 20

Abstract

This paper reports the synthesis of the alkaloid natural product (±)-cylindricine C, in addition to a formal synthesis of (±)-cylindricine A. The key step in our sequence is the (ipso) regioselective addition of an alkyl Grignard reagent to a C-2 substituted pyridinium salt to generate the dihydropyridone core of the alkaloid targets. After cyclisation to form the A and C rings of the cyclindricines the net outcome is a short (13 steps) synthesis of this natural ...