Efficient synthesis of propargylic ethers under the DBU conditions and its application to natural products synthesis

T Yokoyama, N Kutsumura, T Ohgiya…

Index: Yokoyama, Tadashi; Kutsumura, Noriki; Ohgiya, Tadaaki; Nishiyama, Shigeru Bulletin of the Chemical Society of Japan, 2007 , vol. 80, # 3 p. 578 - 582

Full Text: HTML

Citation Number: 13

Abstract

Conversion of dibromides carrying O-functional groups at adjacent positions to the corresponding propargylic ethers was successfully carried out under the DBU conditions through 2-bromo-1-alkenes as intermediates. The optically active γ-lactone-class natural products, such as (−)-muricatacin (4) and (R, R)-sapinofuranone B (5) were synthesized using the propargylic ether intermediate produced by the elimination reaction mentioned ...