Unusual biomimetic oxidations of indoles: synthesis of suaveoline and an alkaloid G analogue

被引：9

作者：

Bailey, PD ^{[1
]}

Morgan, KM ^{[1
]}

Rosair, GM ^{[1
]}

Thomas, RL ^{[1
]}

机构：

[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 47期

关键词：

alkaloids; indoles; oxidation;

D O I：

10.1016/S0040-4039(99)01684-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8255 / 8259

页数：5

共 14 条

[1] AJMALINE .1. [J].

ANET, FAL ;

CHAKRAVARTI, D ;

ROBINSON, R ;

SCHLITTLER, E .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (APR) :1242-1260

[2] A total asymmetric synthesis of (-)-suaveoline [J].

Bailey, PD ;

Morgan, KM .

CHEMICAL COMMUNICATIONS, 1996, (12) :1479-1480

[3] New asymmetric route to bridged indole alkaloids: Formal enantiospecific syntheses of (-)-suaveoline, (-)-raumacline and (-)-N-b-methylraumacline [J].

Bailey, PD ;

Collier, ID ;

Hollinshead, SP ;

Moore, MH ;

Morgan, KM ;

Smith, DI ;

Vernon, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (08) :1209-1214

[4] AN ASYMMETRIC ROUTE TO THE DEMETHOXY-FUMITREMORGINS [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR ;

EVERETT, JH ;

REYNOLDS, CD ;

WOOD, SD ;

GIORDANO, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :451-458

[5] ENHANCING THE YIELD AND DIASTEREOSELECTIVITY OF THE PICTET-SPENGLER REACTION - A HIGHLY EFFICIENT ROUTE TO CIS-1,3-DISUBSTITUTED TETRAHYDRO-BETA-CARBOLINES [J].

BAILEY, PD ;

MOORE, MH ;

MORGAN, KM ;

SMITH, DI ;

VERNON, JM .

TETRAHEDRON LETTERS, 1994, 35 (21) :3587-3588

[6] DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY IN THE PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR ;

MORGAN, K ;

PALMER, SJ ;

PRINCE, SN ;

REYNOLDS, CD ;

WOOD, SD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :431-439

[7] EXCEPTIONAL STEREOCHEMICAL CONTROL IN THE PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR .

TETRAHEDRON LETTERS, 1987, 28 (43) :5177-5180

[8] USE OF THE KINETICALLY CONTROLLED PICTET-SPENGLER REACTION IN THE ASYMMETRIC-SYNTHESIS OF INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-AJMALINE, (-)-KOUMINE, (-)-TABERPSYCHINE, (-)-KOUMIDINE AND (-)-SUAVOLINE [J].

BAILEY, PD ;

MCLAY, NR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :441-449

[9] ALKALOIDS FROM RAUWOLFIA-SERPENTINA CELL-CULTURES TREATED WITH AJMALINE [J].

ENDRESS, S ;

TAKAYAMA, H ;

SUDA, S ;

KITAJIMA, M ;

AIMI, N ;

SAKAI, SI ;

STOCKIGT, J .

PHYTOCHEMISTRY, 1993, 32 (03) :725-730

[10] GENERAL-APPROACH FOR THE SYNTHESIS OF AJMALINE-RELATED ALKALOIDS - ENANTIOSPECIFIC TOTAL SYNTHESIS OF (-)-SUAVEOLINE, (-)-RAUMACLINE, AND (-)-NB-METHYLRAUMACLINE [J].

FU, XY ;

COOK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :661-672

← 1 2 →