A STEREOSELECTIVE TOTAL SYNTHESIS OF DASYCARPIDAN ALKALOIDS - (+/-)-DASYCARPIDONE, (+/-)-DASYCARPIDOL AND (+/-)-NORDASYCARPIDONE

被引：11

作者：

BONJOCH, J

CASAMITJANA, N

GRACIA, J

BOSCH, J

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 23期

关键词：

D O I：

10.1039/c39910001687

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective total synthesis of the dasycarpidan alkaloids dasycarpidone 1, dasycarpidol 2 and nordasycarpidone 3 has been achieved from the tetracyclic intermediate 6, the key step being the oxidation of the C-6 methylene group.

引用

页码：1687 / 1688

页数：2

共 10 条

[1] SYNTHESES IN THE ELLIPTICINE-OLIVACINE SERIES - A POSSIBLE BIOGENETIC MODEL [J].

BESSELIEVRE, R ;

HUSSON, HP .

TETRAHEDRON, 1981, 37 :241-246

[2] STEREOCONTROLLED ACCESS TO DASYCARPIDAN-TYPE COMPOUNDS AND FORMAL TOTAL SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS OF THE STRYCHNAN-TYPE [J].

BONJOCH, J ;

CASAMITJANA, N ;

GRACIA, J ;

BOSCH, J .

TETRAHEDRON LETTERS, 1989, 30 (41) :5659-5662

[3] SYNTHETIC APPLICATIONS OF "2-CYANO-1,2,3,6-TETRAHYDROPYRIDINES .2. SYNTHESIS OF ISODASYCARPIDONE AND RELATED SYSTEMS, THE ERVITSINE SKELETON, AND ITS BENZO ANALOG [J].

BOSCH, J ;

RUBIRALTA, M ;

DOMINGO, A ;

BOLOS, J ;

LINARES, A ;

MINGUILLON, C ;

AMAT, M ;

BONJOCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1516-1522

[4] TOTAL SYNTHESIS OF (+/-)-DASYCARPIDONE, (+/-)-EPIDASYCARPIDONE, AND (+/-)-EPIULEINE [J].

DOLBY, LJ ;

BIERE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3843-&

[5] SYNTHESES OF (+)-DASYCARPIDONE, (+)-3-EPI-DASYCARPIDONE, (+)-ULEINE AND (+)-3-EPI-ULEINE [J].

JACKSON, A ;

WILSON, NDV ;

GASKELL, AJ ;

JOULE, JA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (19) :2738-&

[6] ALKALOID STUDIES .53. STRUCTURES OF 9 NEW ALKALOIDS FROM ASPIDOSPERMA DASYCARPON A DC [J].

JOULE, JA ;

OHASHI, M ;

GILBERT, B ;

DJERASSI, C .

TETRAHEDRON, 1965, 21 (07) :1717-+

[7]

KAMETANI T, 1971, CHEM PHARM BULL, V19, P1424

[8] STUDIES ON SYNTHESES OF HETEROCYCLIC COMPOUNDS .394. TOTAL SYNTHESES OF (+/-)-DASYCARPIDONE AND (+/-)-3-EPIDASYCARPIDONE - FORMAL TOTAL SYNTHESES OF (+/-)-ULEINE AND (+/-)-3-EPIULEINE [J].

KAMETANI, T ;

SUZUKI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (09) :1291-&

[9]

KOTHA S, 1990, J ORG CHEM, V55, P3858

[10]

SUNDBERG RJ, 1970, CHEM INDOLES, P282

← 1 →