Total synthesis of (±)-chartelline C

被引：73

作者：

Baran, Phil S. ^{[1
]}

Shenvi, Ryan A. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 43期

关键词：

BRYOZOAN CHARTELLA-PAPYRACEA; BETA-LACTAM ALKALOIDS; MARINE BRYOZOAN; CONSTRUCTION; MODEL;

D O I：

10.1021/ja0659673

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of (±)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive β-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation. Copyright © 2006 American Chemical Society.

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页码：14028 / 14029

页数：2

相关论文

共 22 条

[1] MARINE ALKALOIDS .12. CHARTELLINES, HALOGENATED BETA-LACTAM ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].

ANTHONI, U ;

CHEVOLOT, L ;

LARSEN, C ;

NIELSEN, PH ;

CHRISTOPHERSEN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4709-4712

[2] Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].

Baran, PS ;

Richter, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396

[3] A remarkable ring contraction en route to the chartelline alkaloids [J].

Baran, PS ;

Shenvi, RA ;

Mitsos, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (24) :3714-3717

[4]

CHAFFE SC, 2001, THESIS YALE U

[5] MARINE ALKALOIDS .10. CHARTELLINE-A - A PENTAHALOGENATED ALKALOID FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].

CHEVOLOT, L ;

CHEVOLOT, AM ;

GAJHEDE, M ;

LARSEN, C ;

ANTHONI, U ;

CHRISTOPHERSEN, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4542-4543

[6] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].

DIECK, HA ;

HECK, FR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263

[7] Indol-2-one intermediates:: Mechanistic evidence and synthetic utility.: Total syntheses of (±)-flustramines A and C [J].

Fuchs, JR ;

Funk, RL .

ORGANIC LETTERS, 2005, 7 (04) :677-680

[8] A STEREOSELECTIVE TRANSFORMATION OF PSEUDOINDOXYLS INTO OXINDOLES IN A SINGLE OPERATION [J].

GULLER, R ;

BORSCHBERG, HJ .

TETRAHEDRON LETTERS, 1994, 35 (06) :865-868

[9] FLOW THERMOLYSIS REARRANGEMENTS IN THE INDOLE ALKALOID SERIES - 1,2-DEHYDROASPIDOSPERMIDINE [J].

HUGEL, G ;

ROYER, D ;

SIGAUT, F ;

LEVY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4631-4636

[10] Efficient construction of the securine A carbon skeleton [J].

Korakas, P ;

Chaffee, S ;

Shotwell, JB ;

Duque, P ;

Wood, JL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :12054-12057