A scalable route to trisubstituted (E)-vinyl bromides

被引：13

作者：

Cho, CG ^{[1
]}

Kim, WS

Smith, AB

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol051376q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

引用

收藏

页码：3569 / 3572

页数：4

相关论文

共 30 条

[1] Synthesis of microcolin B, a potent new immunosuppressant using an efficient mixed imide formation reaction [J].

Andrus, MB ;

Li, WK ;

Keyes, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5542-5549

[2]

[Anonymous], [No title captured]

[3] Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A [J].

Archibald, SC ;

Barden, DJ ;

Bazin, JFY ;

Fleming, I ;

Foster, CF ;

Mandal, AK ;

Mandal, AK ;

Parker, D ;

Takaki, K ;

Ware, AC ;

Williams, ARB ;

Zwicky, AB .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (07) :1051-1064

[4] Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].

Betzer, JF ;

Delaloge, F ;

Muller, B ;

Pancrazi, A ;

Prunet, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780

[5] SYNTHESIS OF THE POLYETHER ANTIBIOTIC MONENSIN .2. PREPARATION OF INTERMEDIATES [J].

COLLUM, DB ;

MCDONALD, JH ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2118-2120

[6] First total synthesis of (±)-taxifolial A and (±)-iso-caulerpenyne [J].

Commeiras, L ;

Santelli, M ;

Parrain, JL .

ORGANIC LETTERS, 2001, 3 (11) :1713-1715

[7]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[8] Enantioselective total synthesis of borrelidin [J].

Duffey, MO ;

LeTiran, A ;

Morken, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1458-1459

[9] Versatile enantiocontrolled synthesis of (+)-flostriecin [J].

Esumi, T ;

Okamoto, N ;

Hatakeyama, S .

CHEMICAL COMMUNICATIONS, 2002, (24) :3042-3043

[10] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES [J].

FLEMING, I ;

NEWTON, TW ;

ROESSLER, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2527-2532