Formal synthesis of (-)-aphanorphine using seqnential photomediated radical reactions of dithiocarbamates

被引：79

作者：

Grainger, Richard S. ^{[1
]}

Welsh, Emma J. ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclization; metathesis; oxidation; radical reactions; sulfinamides;

D O I：

10.1002/anie.200701055

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Time to change the light bulb: An alkyl dithiocarbamate, itself formed through a photoinitiated group-transfer cyclization of a carbamoyl radical, undergoes a second photomediated radical process initiated with a different light source. These two reactions, which proceed through the same cyclohexenyl radical intermediate, are key steps in a new asymmetric synthesis of the alkaloid aphanorphine. TEMPO = 2,2,6,6-tetramethyl-1-piperidinoxyl radical. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5377 / 5380

页数：4

共 62 条

[51] ENANTIOCONTROLLED SYNTHESIS OF (+)-APHANORPHINE FROM (R)-O-BENZYLGLYCIDOL - ASSIGNMENT OF ABSOLUTE-CONFIGURATION [J].

TAKANO, S ;

INOMATA, K ;

SATO, T ;

OGASAWARA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (21) :1591-1592

[52] THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF NATURAL (-)-APHANORPHINE [J].

TAKANO, S ;

INOMATA, K ;

SATO, T ;

TAKAHASHI, M ;

OGASAWARA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (04) :290-292

[53] Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization [J].

Tamura, O ;

Yanagimachi, T ;

Ishibashi, H .

TETRAHEDRON-ASYMMETRY, 2003, 14 (19) :3033-3041

[54] Synthesis of (-)-aphanorphine using aryl radical cyclization [J].

Tamura, O ;

Yanagimachi, T ;

Kobayashi, T ;

Ishibashi, H .

ORGANIC LETTERS, 2001, 3 (16) :2427-2429

[55] 7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as asynthetic equivalent of ketodicyclopentadiene: a new route to (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine [J].

Tanaka, K ;

Taniguchi, T ;

Ogasawara, K .

TETRAHEDRON LETTERS, 2001, 42 (06) :1049-1052

[56] An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine [J].

Taylor, SK ;

Ivanovic, M ;

Simons, LJ ;

Davis, MM .

TETRAHEDRON-ASYMMETRY, 2003, 14 (06) :743-747

[57] A novel synthesis of functional dithioesters, dithiocarbamates, xanthates and trithiocarbonates [J].

Thang, SH ;

Chong, YK ;

Mayadunne, RTA ;

Moad, G ;

Rizzardo, E .

TETRAHEDRON LETTERS, 1999, 40 (12) :2435-2438

[58] Remarkable control of radical cyclization processes of cyclic enyne:: Total syntheses of (±)-methyl gummiferolate, (±)-methyl 7β-hydroxykaurenoate, and (±)-methyl 7-oxokaurenoate and formal synthesis of (±)-gibberellin A12 from a common synthetic precursor [J].

Toyota, M ;

Yokota, M ;

Ihara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :1856-1861

[59] Construction of bicyclo[2.2.2]octane ring system via homoallyl-homoallyl radical rearrangement [J].

Toyota, M ;

Yokota, M ;

Ihara, M .

TETRAHEDRON LETTERS, 1999, 40 (08) :1551-1554

[60] (R-S)-(+)-2-METHYL-2-PROPANESULFINAMIDE [tert-Butanesulfinamide] [J].

Weix, Daniel J. ;

Ellman, Jonathan A. .

ORGANIC SYNTHESES, 2005, 82 :157-+

← 1 2 3 4 5 6 7 →