Organic Letters
Organic Letters
5 years ago

A Chiral Pentenolide-Based Unified Strategy toward Dihydrocorynantheal, Dihydrocorynantheol, Protoemetine, Protoemetinol, and Yohimbane

A Chiral Pentenolide-Based Unified Strategy toward Dihydrocorynantheal, Dihydrocorynantheol, Protoemetine, Protoemetinol, and Yohimbane
Ran Hong, Lili Zhu, Changmin Xie, Yan Zhang, Jisheng Luo
An organocatalytic cross-aldol reaction of formaldehyde (formalin) with alkyl aldehydes, followed by the Z-selective Horner–Wadsworth–Emmons (HWE) reaction and immediate lactonization, afforded γ-alkylated pentenolides in good overall yields and excellent enantioselectivities. Based on this scalable sequence, five quinolizidine alkaloids were synthesized in a unified and concise manner. The development of an in situ activation of a tertiary amide to improve the efficiency of the Bischler–Napieraiski (B–N) reaction was also noteworthy due to the generality to sensitive substrates for a variety of target molecules.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01573

DOI: 10.1021/acs.orglett.7b01573

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