SYNTHESIS OF A TETRACYCLIC SUBSTRUCTURE OF MANZAMINE-A

被引：51

作者：

CAMPBELL, JA ^{[1
]}

HART, DJ ^{[1
]}

机构：

[1] OHIO STATE UNIV,DEPT CHEM,120 W 18TH AVE,COLUMBUS,OH 43210

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)60944-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of tetracyclic manzamine A substructure 28 is described. The route involves (1) a new approach to perhydroisoquinolines, (2) a Mitsunobu reaction that proceeds with net retention of configuration using a new N-acyl sulfonamide (16) and (3) a high yield preparation of a DELTA3,4-azocine via an intramolecular N-alkylation.

引用

页码：6247 / 6250

页数：4

共 34 条

[1] BALDWIN JE, 1992, TETRAHEDRON LETT, P2059
[2] BASHA A, 1977, SYN COMMUN, P549
[3] SYNTHESIS OF THE TRICYCLIC HEART OF MANZAMINES
BRANDS, KMJ
PANDIT, UK
[J]. TETRAHEDRON LETTERS, 1989, 30 (11) : 1423 - 1426
[4] SYNTHESIS OF THE HOMOCHIRAL TRICYCLIC HEART OF MANZAMINE-A
BRANDS, KMJ
MEEKEL, AAP
PANDIT, UK
[J]. TETRAHEDRON, 1991, 47 (10-11) : 2005 - 2026
[5] MACRO RINGS .13. SYNTHESIS AND PROPERTIES OF 1,7-CYCLODODECADIYNE AND RELATED COMPOUNDS
CRAM, DJ
ALLINGER, NL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (11) : 2518 - 2524
[6] SYNTHESIS OF THE PYRROLO[2,3-I]ISOQUINOLINE SUBSTRUCTURE OF THE MANZAMINE FAMILY OF ALKALOIDS
HART, DJ
MCKINNEY, JA
[J]. TETRAHEDRON LETTERS, 1989, 30 (20) : 2611 - 2614
[7] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES
HENRY, JR
MARCIN, LR
MCINTOSH, MC
SCOLA, PM
HARRIS, GD
WEINREB, SM
[J]. TETRAHEDRON LETTERS, 1989, 30 (42) : 5709 - 5712
[8] 4-DIALKYLAMINOPYRIDINES AS ACYLATION CATALYSTS .4. 4-DIALKYLAMINOPYRIDINES AS HIGHLY ACTIVE ACYLATION CATALYSTS
HOFLE, G
STEGLICH, W
VORBRUGGEN, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (08): : 569 - &
[9] IMBROISI DO, 1991, J CHEM SOC P1, P18415
[10] IMBROISI DO, 1989, TETRAHEDRON LETT, P4309

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