TOTAL SYNTHESIS OF THE LYCOPODIUM ALKALOIDS MAGELLANINE AND MAGELLANINONE BY 3-FOLD ANNULATION OF 2-CYCLOPENTENONE

被引：60

作者：

WILLIAMS, JP ^{[1
]}

STLAURENT, DR ^{[1
]}

FRIEDRICH, D ^{[1
]}

PINARD, E ^{[1
]}

RODEN, BA ^{[1
]}

PAQUETTE, LA ^{[1
]}

机构：

[1] OHIO STATE UNIV,EVANS CHEM LABS,COLUMBUS,OH 43210

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 11期

关键词：

D O I：

10.1021/ja00090a017

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereocontrolled synthesis of the complete diquinane-based framework of the two unusual Lycopodium alkaloids magellanine and magellaninone is reported. Michael-Michael ring annulation of the alpha,beta-unsaturated ketone 4 obtained by dehydration of 5a rapidly led to enedione 7, functional group manipulation within which gave rise to 11. Once oxidation to the cyclopentenone had been accomplished, the piperidine ring part structure was incorporated by an unprecedented sequence that ultimately allowed for installation of the requisite cis ring juncture through epimerization. With 17a available, oxidation levels were concisely adjusted with concomitant incorporation of a methyl group to produce magellaninone (2). To complete the route to magellanine (1), 2 was chemoselectively reduced and subjected to a Mitsunobu protocol.

引用

页码：4689 / 4696

页数：8

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