Formal total synthesis of (+)-zaragozic acid C through an Ireland-Claisen rearrangement

被引：31

作者：

Bunte, Jens O. ^{[1
]}

Cuzzupe, Anthony N. ^{[1
]}

Daly, Alica M. ^{[1
]}

Rizzacasa, Mark A. ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Inst Bio21, Melbourne, Vic 3010, Australia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 38期

关键词：

Ireland-Claisen rearrangement; lactones; natural products; total synthesis; zaragozic acid;

D O I：

10.1002/anie.200602507

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A simple rearrangement: A formal total synthesis of zaragozic acid C (1) was achieved by the synthesis of intermediate 2. The key step involves an Ireland-Claisen rearrangement of an allylic ester to generate a carbon-carbon bond and two asymmetric centers simultaneously. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6376 / 6380

页数：5

共 54 条

[1] Recent synthetic studies on the zaragozic acids (squalestatins) [J].

Armstrong, A ;

Blench, TJ .

TETRAHEDRON, 2002, 58 (46) :9321-9349

[2] Total synthesis of (+)-zaragozic acid C [J].

Armstrong, A ;

Barsanti, PA ;

Jones, LH ;

Ahmed, G .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :7020-7032

[3] Total synthesis of (+)-zaragozic acid C [J].

Armstrong, A ;

Jones, LH ;

Barsanti, PA .

TETRAHEDRON LETTERS, 1998, 39 (20) :3337-3340

[4] CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE [J].

BAILEY, WF ;

PUNZALAN, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5404-5406

[5]

BAXTER A, 1992, J BIOL CHEM, V267, P11705

[6] ZARAGOZIC ACIDS - A FAMILY OF FUNGAL METABOLITES THAT ARE PICOMOLAR COMPETITIVE INHIBITORS OF SQUALENE SYNTHASE [J].

BERGSTROM, JD ;

KURTZ, MM ;

REW, DJ ;

AMEND, AM ;

KARKAS, JD ;

BOSTEDOR, RG ;

BANSAL, VS ;

DUFRESNE, C ;

VANMIDDLESWORTH, FL ;

HENSENS, OD ;

LIESCH, JM ;

ZINK, DL ;

WILSON, KE ;

ONISHI, J ;

MILLIGAN, JA ;

BILLS, G ;

KAPLAN, L ;

OMSTEAD, MN ;

JENKINS, RG ;

HUANG, L ;

MEINZ, MS ;

QUINN, L ;

BURG, RW ;

KONG, YL ;

MOCHALES, S ;

MOJENA, M ;

MARTIN, I ;

PELAEZ, F ;

DIEZ, MT ;

ALBERTS, AW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) :80-84

[7] Total synthesis of zaragozic acid A (squalestatin S1). Synthesis of the relay compound [J].

Caron, S ;

Stoermer, D ;

Mapp, AK ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9126-9134

[8] (+)-ZARAGOZIC-ACID-C - SYNTHESIS AND RELATED STUDIES [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8106-8125

[9] SYNTHESIS OF (+)-ZARAGOZIC ACID-C [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10825-10826

[10] Enantiospecific synthesis of the phospholipase A2 inhibitors (-)-cinatrin C1 and (+)-cinatrin C3 [J].

Cuzzupe, AN ;

Di Florio, R ;

White, JM ;

Rizzacasa, MA .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) :3572-3577

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