Total synthesis of (+)-streptazolin

被引：37

作者：

Huang, SL ^{[1
]}

Comins, DL ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 07期

关键词：

D O I：

10.1039/b001425g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first chiral auxiliary mediated asymmetric synthesis of (+)-streptazolin has been accomplished in 13 steps and with a high degree of stereocontrol.

引用

页码：569 / 570

页数：2

共 19 条

[1] IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids:: Asymmetric synthesis of (+)-luciduline [J].

Comins, DL ;

Brooks, CA ;

Al-awar, RS ;

Goehring, RR .

ORGANIC LETTERS, 1999, 1 (02) :229-231

[2] Asymmetric synthesis of the Lycopodium alkaloid, Na-acetyl-Nb-methylphlegmarine [J].

Comins, DL ;

Libby, AH ;

Al-awar, RS ;

Foti, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2184-2185

[3] EFFICIENT SYNTHESIS AND RESOLUTION OF TRANS-2-(1-ARYL-1-METHYLETHYL)CYCLOHEXANOLS - PRACTICAL ALTERNATIVES TO 8-PHENYLMENTHOL [J].

COMINS, DL ;

SALVADOR, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4656-4661

[4] Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts [J].

Comins, DL ;

Kuethe, JT ;

Hong, H ;

Lakner, FJ ;

Concolino, TE ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2651-2652

[5]

COMMINS DL, 1994, J AM CHEM SOC, V116, P4719

[6] METABOLISM PRODUCTS OF MICROORGANISMS .205. ISOLATION AND STRUCTURE OF STREPTAZOLIN [J].

DRAUTZ, H ;

ZAHNER, H ;

KUPFER, E ;

KELLERSCHIERLEIN, W .

HELVETICA CHIMICA ACTA, 1981, 64 (06) :1752-1765

[7] ENANTIOSELECTIVE TOTAL SYNTHESIS OF STREPTAZOLIN - THE TANDEM USE OF IMINIUM ION VINYLSILANE CYCLIZATIONS AND INTRAMOLECULAR ACYLATIONS [J].

FLANN, CJ ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6115-6118

[8] NEW LEAD STRUCTURES BY DIELS-ALDER REACTIONS OF STREPTAZOLIN WITH NAPHTHOQUINONES [J].

GRABLEY, S ;

KLUGE, H ;

HOPPE, HU .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (07) :664-665

[9] HETEROCYCLE SYNTHESIS BY PALLADIUM-CATALYZED CYCLIZATION-ANION CAPTURE PROCESSES - A POWERFUL NEW STRATEGY [J].

GRIGG, R .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (03) :631-639

[10]

Han G, 2000, ANGEW CHEM INT EDIT, V39, P237, DOI 10.1002/(SICI)1521-3773(20000103)39:1<237::AID-ANIE237>3.0.CO

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