Bioactive Montanine Derivatives from Halide-induced Rearrangements of Haemanthamine-type Alkaloids. Absolute Configuration by VCD

被引：42

作者：

Cedron, Juan C. ^{[1
,2
]}

Estevez-Braun, Ana ^{[1
,2
]}

Ravelo, Angel G. ^{[1
,2
]}

Gutierrez, David

Flores, Ninoska

Bucio, Maria A. ^{[3
]}

Perez-Hernandez, Nury ^{[4
]}

Joseph-Nathan, Pedro ^{[3
]}

机构：

[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Spain

[2] Univ Mayor San Andres, Fac Ciencias Farmaceut & Bioquim, Inst Invest Farmaco Bioquim, ICIC, Miraflores La Paz, Bolivia

[3] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

[4] Univ Autonoma Estado Hidalgo, Escuela Med, Pachuca 42001, Hidalgo, Mexico

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 07期

关键词：

VIBRATIONAL CIRCULAR-DICHROISM; FORMAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; AMARYLLIDACEAE ALKALOIDS; NARCISSUS ALKALOIDS; (+/-)-PANCRACINE; (-)-BRUNSVIGINE; CYCLOADDITION; CYCLIZATION; ROUTE;

D O I：

10.1021/ol900065x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity.

引用

页码：1491 / 1494

页数：4