Synthesis of Marasin and 9-Me-Marasin,(Nona-and Deca-6, 8-diyne-3, 4-dienol).

W de Graaf, A Smits, J Boersma, G van Koten…

Index: De Graaf; Smits; Boersma; Van Koten Tetrahedron, 1988 , vol. 44, # 21 p. 6699 - 6704

Full Text: HTML

Citation Number: 31

Abstract

3, 4-Pentadienol was protected with ethyl vinyl ether and regioselectively (70%) deprotonated at the terminal position by treatment with BuLi in THF at low temperature. Starting from the so obtained lithium compound, Marasin (nona-6, 8-diyne-3, 4-dienol)(1a) and 9-Me-Marasin (deca-6, 8-diyne-3, 4-dienol)(1b) were prepared by two metal-mediated synthetic routes. Route A involves transmetallation of the lithium compound with LiCuBr2, ...