Organic Letters
Organic Letters
4 years ago

Asymmetric Syntheses of Amaryllidaceae Alkaloids (−)-Crinane and (+)-4a-Dehydroxycrinamabine

Asymmetric Syntheses of Amaryllidaceae Alkaloids (−)-Crinane and (+)-4a-Dehydroxycrinamabine
Da-Yu Wang, Yong-Qiang Wang, Ya-Ru Gao
A palladium-catalyzed asymmetric allyl–allyl cross-coupling reaction to construct the chiral quaternary carbon center of crinane alkaloids has been developed. On the basis of an efficient approach, the enantioselective synthesis of (−)-crinane (1) is presented, and the first asymmetric total synthesis of (+)-4a-dehydroxycrinamabine (2) was achieved by subsequent oxidation, 1,4-conjugate addition, RCM reaction, reductive amination, and Pictet–Spengler reaction. The method provided an alternative strategy for the syntheses of crinane alkaloids and other Amaryllidaceae natural products.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01486

DOI: 10.1021/acs.orglett.7b01486

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