The manganese-mediated regioselective chlorination of allenes in synthetic approaches towards the spongistatins and halomon natural products

被引：21

作者：

Boyes, AL ^{[1
]}

Wild, M ^{[1
]}

机构：

[1] Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 37期

关键词：

allenes; dienes; halogenation;

D O I：

10.1016/S0040-4039(98)01410-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples for the chlorination of allenes using manganese reagents generated from potassium permanganate and benzyl triethylammonium chloride in the presence of the chlorine donors oxalyl chloride or chlorotrimethylsilane are reported with the aim of developing useful synthetic routes to the spongistatin and halomon marine natural products. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6725 / 6728

页数：4

共 20 条

[1] Palladium-catalyzed 1,2-oxidation of allenes [J].

Backvall, JE ;

Jonasson, C .

TETRAHEDRON LETTERS, 1997, 38 (02) :291-294

[2] STEREOCHEMISTRY OF ADDITION REACTIONS OF ALLENES .5. STEREOSELECTIVE BROMINATION OF 1,2-CYCLONONADIENE [J].

BYRD, LR ;

CASERIO, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (22) :5758-&

[3] PHOTOCHEMICAL-SYNTHESIS OF DECIPIENE DITERPENES [J].

DAUBEN, WG ;

SHAPIRO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4252-4258

[4] Enantioselective synthesis of altohyrtin C (spongistatin 2): Synthesis of the AB- and CD-spiroketal subunits [J].

Evans, DA ;

Coleman, PJ ;

Dias, LC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2738-2741

[5] ISOLATION AND STRUCTURE-ACTIVITY FEATURES OF HALOMON-RELATED ANTITUMOR MONOTERPENES FROM THE RED ALGA PORTIERIA-HORNEMANNII [J].

FULLER, RW ;

CARDELLINA, JH ;

JUREK, J ;

SCHEUER, PJ ;

ALVARADOLINDNER, B ;

MCGUIRE, M ;

GRAY, GN ;

STEINER, JR ;

CLARDY, J ;

MENEZ, E ;

SHOEMAKER, RH ;

NEWMAN, DJ ;

SNADER, KM ;

BOYD, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (25) :4407-4411

[6] A PENTAHALOGENATED MONOTERPENE FROM THE RED ALGA PORTIERIA-HORNEMANNII PRODUCES A NOVEL CYTOTOXICITY PROFILE AGAINST A DIVERSE PANEL OF HUMAN TUMOR-CELL LINES [J].

FULLER, RW ;

CARDELLINA, JH ;

KATO, Y ;

BRINEN, LS ;

CLARDY, J ;

SNADER, KM ;

BOYD, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (16) :3007-3011

[7] BIOACTIVE MARINE METABOLITES .48. CINACHYROLIDE-A - A POTENT CYTOTOXIC MACROLIDE POSSESSING 2 SPIRO KETALS FROM MARINE SPONGE CINACHYRA SP [J].

FUSETANI, N ;

SHIMODA, K ;

MATSUNAGA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3977-3981

[8]

Guo JS, 1998, ANGEW CHEM INT EDIT, V37, P187, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<187::AID-ANIE187>3.0.CO

[9]

2-D

[10] Synthesis of several naturally occurring polyhalogenated monoterpenes of the Halomon class [J].

Jung, ME ;

Parker, MH .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7094-7095

← 1 2 →