A remarkable ring contraction en route to the chartelline alkaloids

被引：58

作者：

Baran, PS ^{[1
]}

Shenvi, RA ^{[1
]}

Mitsos, CA ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 24期

关键词：

D O I：

10.1002/anie.200500522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Weinheim (Chemical Equation Presented) One-of-a-kind. A bromine-induced rearrangement has been designed for the formation of the spiro-β-lactam ring present in the structurally unique chartelline alkaloids (see picture of chartelline A). This method is used in combination with others to provide rapid access to the carbocyclic skeletons of the chartelline, securine, and securamine alkaloids. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：3714 / 3717

页数：4

相关论文

共 38 条

[1]

[Anonymous], 2005, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200461864

[2] CHARTELLAMIDE-A AND CHARTELLAMIDE-B, HALOGENATED BETA-LACTAM INDOLE IMIDAZOLE ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].

ANTHONI, U ;

BOCK, K ;

CHEVOLOT, L ;

LARSEN, C ;

NIELSEN, PH ;

CHRISTOPHERSEN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (25) :5638-5639

[3] 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

[4] Short, enantioselective total synthesis of Stephacidin A [J].

Baran, PS ;

Guerrero, CA ;

Ambhaikar, NB ;

Hafensteiner, BD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :606-609

[5] A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].

Baran, PS ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905

[6] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[7]

CHAFFEE SC, 2001, THESIS YALE U

[8] 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

[9]

COULADOUROS EA, COMMUNICATION

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

DIECK, HA ;

HECK, FR .

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

← 1 2 3 4 →