Efficient synthesis of (-)-(R)-muscone by enantioselective protonation

被引：29

作者：

Fehr, C ^{[1
]}

Galindo, J ^{[1
]}

Farris, I ^{[1
]}

Cuenca, A ^{[1
]}

机构：

[1] Firmenich SA Corp, Div Res & Dev, CH-1211 Geneva 8, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2004年 / 87卷 / 07期

关键词：

D O I：

10.1002/hlca.200490157

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 --> (S)-4 in Scheme 2) is presented. The C-15 macrocyclic system is obtained by ozonolysis (Scheme 7).

引用

页码：1737 / 1747

页数：11

共 43 条

[1]

Alexakis A, 1999, SYNLETT, P1811

[2]

[Anonymous], PERFUMESART SCI TECH

[3] ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE [J].

ARAI, Y ;

KAWANAMI, S ;

KOIZUMI, T .

CHEMISTRY LETTERS, 1990, (09) :1585-1586

[4] Efficient asymmetric protonation of enolates with readily accessible chiral α-sulfinyl alcohols [J].

Asensio, G ;

Alemán, P ;

Cuenca, A ;

Gil, J ;

Medio-Simón, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :4073-4078

[5] CHIRAL ECONOMIC SYNTHESIS OF (R)-MUSCONE AND (S)-MUSCONE USING CYCLOFRAGMENTATION OF EPOXYSULFONES [J].

BRANCA, Q ;

FISCHLI, A .

HELVETICA CHIMICA ACTA, 1977, 60 (03) :925-944

[6] Copper-catalyzed conjugate addition on macrocyclic, cyclic, and acyclic enones with a chiral phosphoramidite ligand having a C2-symmetric amine moiety [J].

Choi, YH ;

Choi, JY ;

Yang, HY ;

Kim, YH .

TETRAHEDRON-ASYMMETRY, 2002, 13 (08) :801-804

[7] SYNTHETICALLY USEFUL BETA-LITHIOALKOXIDES FROM REDUCTIVE LITHIATION OF EPOXIDES BY AROMATIC RADICAL-ANIONS [J].

COHEN, T ;

JEONG, IH ;

MUDRYK, B ;

BHUPATHY, M ;

AWAD, MMA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1528-1536

[8] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS [J].

COREY, EJ ;

WINTER, RAE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) :2677-&

[9] OCCURRENCE AND ORIGIN OF A PRONOUNCED DIRECTING EFFECT OF A HYDROXYL GROUP IN HYDROGENATION WITH [IR(COD)P-C-HX3(PY)]PF6 [J].

CRABTREE, RH ;

DAVIS, MW .

ORGANOMETALLICS, 1983, 2 (05) :681-682

[10] DERIVATIVES OF ORTHOACIDS .2. PREPARATION OF OLEFINS FROM 1,2-DIOLS [J].

CRANK, G ;

EASTWOOD, FW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (12) :1392-&

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