Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (-)-ambrox and (+)-zonarol

被引：44

作者：

Akita, H ^{[1
]}

Nozawa, M ^{[1
]}

Shimizu, H ^{[1
]}

机构：

[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(98)00172-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Stereoselective syntheses of (-)-ambrox 2 and (+)-zonarol 3 were achieved based on the enzymatic syntheses of (8aS)- and (8aR)-decalin-type 1,3-diols 1, respectively. Non-racemic intermediates such as (8aS)-1 and (8aR)-1 were obtained based on the enantioselective hydrolyses of the phenolic acetal derivative (+/-)-7 by acylase I. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1789 / 1799

页数：11

共 21 条

[1]

Akita H, 1997, CHEM PHARM BULL, V45, P824

[2] FORMAL SYNTHESIS OF (+/-)-AMBROX(R) [J].

BARCO, A ;

BENETTI, S ;

BIANCHI, A ;

CASOLARI, A ;

GUARNERI, M ;

POLLINI, GP .

TETRAHEDRON, 1995, 51 (30) :8333-8338

[3] SYNTHESIS OF AMBROX(R) FROM (-)-SCLAREOL AND (+)-CIS-ABIENOL [J].

BARRERO, AF ;

ALVAREZMANZANEDA, EJ ;

ALTAREJOS, J ;

SALIDO, S ;

RAMOS, JM .

TETRAHEDRON, 1993, 49 (45) :10405-10412

[4] SYNTHESIS OF AMBROX(R) FROM COMMUNIC ACIDS [J].

BARRERO, AF ;

ALTAREJOS, J ;

ALVAREZMANZANEDA, EJ ;

RAMOS, JM ;

SALIDO, S .

TETRAHEDRON, 1993, 49 (28) :6251-6262

[5] AN IMPROVED SYNTHESIS OF (-)-DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTHO[2,1-B]FURAN VIA OZONOLYSIS OF (-)-SCLAREOL [J].

BARTON, DHR ;

TAYLOR, DK ;

TSE, C .

TETRAHEDRON LETTERS, 1994, 35 (51) :9505-9508

[6] AN EFFICIENT SYNTHESIS OF (-)-DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTHOL[2,1-B]FURAN FROM (-)-SCLAREOL [J].

BARTON, DHR ;

PAREKH, SI ;

TAYLOR, DK ;

TSE, CI .

TETRAHEDRON LETTERS, 1994, 35 (32) :5801-5804

[7] THE SYNTHESIS OF RACEMIC AMBROX [J].

BUCHI, G ;

WUEST, H .

HELVETICA CHIMICA ACTA, 1989, 72 (05) :996-1000

[8] SYNTHESIS OF AMBERGRIS FRAGRANCE CHEMICALS FROM SCLAREOL, INVOLVING PALLADIUM CATALYZED KEY STEPS [J].

COSTEMANIERE, IC ;

ZAHRA, JP ;

WAEGELL, B .

TETRAHEDRON LETTERS, 1988, 29 (09) :1017-1020

[9] A SHORT SYNTHESIS OF AMBROX FROM SCLAREOL [J].

DECORZANT, R ;

VIAL, C ;

NAF, F ;

WHITESIDES, GM .

TETRAHEDRON, 1987, 43 (08) :1871-1879

[10] REDUCTION WITH METAL HYDRIDES .12. REDUCTION OF ACETALS AND KETALS WITH LITHIUM ALUMINUM HYDRIDE-ALUMINUM CHLORIDE [J].

ELIEL, EL ;

BADDING, VG ;

RERICK, MN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (12) :2371-&

← 1 2 3 →