Chemical communications

Asymmetric synthesis of avenaciolide via cascade palladium catalysed cyclisation–carbonylation of bromodienes

VK Aggarwal, PW Davies, AT Schmidt

文献索引：Aggarwal, Varinder K.; Davies, Paul W.; Schmidt, Andreas T. Chemical Communications, 2004 , # 10 p. 1232 - 1233

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被引用次数: 1

摘要

Our synthesis began with Sharpless epoxidation 10 of allylic alcohol 7 followed by conversion to allylic alcohol 8 using the protocol developed by Ibuka et al. 11 The alcohol 8 was formed in high enantioselectivity (90% ee). Alternative approaches starting from nonanal and using asymmetric addition of divinyl zinc 12 or zinc catalysed addition of 2-methyl-3-butyn-2-ol 13 with N-methylephedrine as chiral ligand gave both lower enantioselectivities and lower yields.