SYNTHETIC STUDIES TOWARDS PASPALICINE - PRELIMINARY INVESTIGATIONS, AND THE SYNTHESIS OF 3',4',7',7'A,9',10',11',11'A-OCTAHYDRO-4',4',7'A-TRIMETHYLSPIRO[1,3-DIOXOLANE]-2,8'(6'H)-2'H-3',5'A-EPOXYNAPHTH [2,1-B]OXEPIN-2'-ONE

被引：13

作者：

ALI, A ^{[1
]}

GUILE, SD ^{[1
]}

SAXTON, JE ^{[1
]}

THORNTONPETT, M ^{[1
]}

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 32期

关键词：

INDOLE-DITERPENE MOLD METABOLITES; PASPALICINE; BETA-PYRONE FORMATION; KETALIZATION; X-RAY CRYSTAL STRUCTURE DETERMINATION;

D O I：

10.1016/S0040-4020(01)86569-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preliminary investigations directed towards the synthesis of the indole-diterpene mould metabolite, paspalicine 1, are described. Following the preparation of the beta-pyrone ketal 7, which contains the characteristic functional group of paspalicine, the compound 25, which constitutes rings D-G of paspalicine with the correct relative stereochemistry, has been synthesised in eight steps from the monoketal 12 of the Wieland-Miescher ketone, in an overall yield of 8%.

引用

页码：6407 / 6426

页数：20

共 24 条

[1] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].