Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G

Journal of the Brazilian Chemical Society

Universidade Estadual de Campinas, Campinas, Brazil¹  Santos, Leonardo S.¹  Pilli, Ronaldo A.¹ 

关键词: homopumiliotoxin 223G;    N-acyliminium ions;    silyloxyfuran;    vinylogous addition;   

DOI  :  10.1590/S0103-50532003000600015

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.

【 授权许可】

Unknown