Quinolizidine alkaloid synthesis via the intramolecular imino diels-alder reaction. epi-lupinine and cryptopleurine

ML Bremmer, NA Khatri…

Index: Bremmer, Martin L.; Khatri, Nazir A.; Weinreb, Steven M. Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3661 - 3666

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Citation Number: 77

Abstract

R= CH, OMe-lj R= CH, Ph-alcohol group of 11 was protected as the methoxymethyl derivative 12. However, all attempts to selectively hydrolyze the dimethyl acetal function of 12 were unsuccessful, and only lactol 14 could be isolated from these reactions. Alcohol 11 was therefore protected instead as the benzyl ether 13 (PhCH2Br, KH, THF; 86%). Acid hydrolysis of 13 afforded the corresponding aldehyde, which without isolation was ...