Synthesis of the acutumine spirocycle via a radical-polar crossover reaction

被引：44

作者：

Li, Fang ^{[1
]}

Castle, Steven L. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 20期

关键词：

D O I：

10.1021/ol701757f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new radical-polar crossover reaction was developed that consists of intramolecular conjugate addition of an aryl radical followed by enolate formation and hydroxylation. A C-C bond, a C-O bond, and two congested stereocenters are created in the process. The product is obtained as a single isomer. The method was used to synthesize the spirocyclic subunit of the alkaloid acutumine.

引用

页码：4033 / 4036

页数：4

共 39 条

[11] SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS (ACYLOINS) - DIRECT OXIDATION OF ENOLATES USING 2-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

VISHWAKARMA, LC ;

BILLMERS, JM ;

FINN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3241-3243

[12] A ONE-STEP PROCEDURE FOR PREPARATION OF TERTIARY ALPHA-KETOLS FROM CORRESPONDING KETONES [J].

GARDNER, JN ;

CARLON, FE ;

GNOJ, O .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (08) :3294-&

[13] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459

[14]

GOTO KAKUJI, 1929, BULL CHEM SOC JAPAN, V4, P220, DOI 10.1246/bcsj.4.220

[15] FACILE SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS BY ENOLATE OXIDATION WITH DIMETHYLDIOXIRANE [J].

GUERTIN, KR ;

CHAN, TH .

TETRAHEDRON LETTERS, 1991, 32 (06) :715-718

[16]

JOHNSON CR, 1994, TETRAHEDRON LETT, V35, P7735, DOI 10.1016/0040-4039(94)80105-3

[17] Total synthesis of (±)-hasubanonine [J].

Jones, Spencer B. ;

He, Liwen ;

Castle, Steven L. .

ORGANIC LETTERS, 2006, 8 (17) :3757-3760

[18] A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides [J].

Krasovskiy, A ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3333-3336

[19] Highly efficient reagents for Br/Mg exchange [J].

Krasovskiy, A ;

Straub, BF ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (01) :159-162

[20] Triethylaluminum- or triethylborane-induced free radical reaction of alkyl iodides and α,β-unsaturated compounds [J].

Liu, JY ;

Jang, YJ ;

Lin, WW ;

Liu, JT ;

Yao, CF .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4030-4038

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