Short Total Synthesis of (-)-Lupinine and (-)-Epiquinamide by Double Mitsunobu Reaction

被引：14

作者：

Silva Santos, Leonardo ^{[1
]}

Mirabal-Gallardo, Yaneris ^{[1
]}

Shankaraiah, Nagula ^{[1
,2
]}

Simirgiotis, Mario J. ^{[3
]}

机构：

[1] Univ Talca, Chem Inst Nat Resources, Lab Asymmetr Synth, Talca, Chile

[2] NIPER, Hyderabad 500037, Andhra Pradesh, India

[3] Univ Antofagasta, Fac Basic Sci, Dept Chem, Lab Nat Prod, Antofagasta, Chile

来源：

SYNTHESIS-STUTTGART | 2011年 / 01期

关键词：

quinolizidine alkaloids; azido reduction; nickel boride; microwave irradiation; Mitsunobu reaction; ENANTIOSELECTIVE TOTAL-SYNTHESIS; N-ACYLIMINIUM IONS; NICKEL BORIDE; AZABICYCLIC ALCOHOLS; CONSTRUCTION; EPIQUINAMIDE; ALKALOIDS; (+)-EPIQUINAMIDE; DERIVATIVES; LUPININE;

D O I：

10.1055/s-0030-1258356

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alternative total syntheses of (-)-lupinine (1) and (-)-epiquinamide (2) have been described via the key intermediate 3 obtained from the addition of 2-trialkylsilyloxyfuran 5 to N-acyliminium intermediate derived from 4. The major R, R-isomer 8 obtained from the Mannich reaction was converted into its R, S-isomer through Mitsunobu reaction. Then, a second Mitsunobu reaction of 3 led to cyano 9 and azido 11 derivatives, which were converted into 1 and 2 in 33 and 36% overall yield from 4, respectively. The synthetic route is amenable for the generation of several quinolizidine alkaloids.

引用

页码：51 / 56

页数：6

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