Tetrahedron

Neat total synthesis of six monoterpenic alkaloids of the actinidine series

N Robert, C Hoarau, F Marsais

Index: Robert, Nicolas; Hoarau, Christophe; Marsais, Francis Tetrahedron, 2007 , vol. 63, # 18 p. 3702 - 3706

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Citation Number: 14

Abstract

A concise enantiopure synthesis of six monoterpenic alkaloids of the actinidine series possessing a cyclopenta [c] pyridine skeleton,(+)-deoxyrhexifoline (4),(+)-boschniakinic acid (5),(+)-boschniakine (6),(−)-plantagonine (7),(−)-indicaine (8) and (−)-tecostidine (9) is reported starting with the chiral precursor 3-bromo-5-((4R)-phenyloxazolin-2-yl) pyridine (10). It involves a C-4 regioselective connection of a butene appendice and an ...