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

被引：24

作者：

BARTON, DHR

PAREKH, SI

TAYLOR, DK

TSE, CI

机构：

[1] Department of Chemistry, Texas A and M University, College Station

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(00)78188-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound 1 was prepared in 74% overall yield (3 steps) from sclareol 2. The key step involves osmium tetroxide catalysed rearrangement to 4a and b during the oxidative degradation of sclareol.

引用

页码：5801 / 5804

页数：4

共 19 条

[1] 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

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

BARRERO, AF ;

ALTAREJOS, J ;

ALVAREZMANZANEDA, EJ ;

RAMOS, JM ;

SALIDO, S .

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

[3] AMBER-TYPE ODORANTS FROM COMMUNIC ACIDS [J].

BARRERO, AF ;

ALTAREJOS, J ;

ALVAREZMANZANEDA, EJ ;

RAMOS, JM ;

SALIDO, S .

TETRAHEDRON, 1993, 49 (42) :9525-9534

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

BUCHI, G ;

WUEST, H .

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

[5] CHEMISTRY OF PODOCARPACEAE .30. CONVERSION OF 8ALPHA,13-EPOXYLABD-14-ENE INTO A COMPOUND WITH AN AMBERGRIS-TYPE ODOUR [J].

CAMBIE, RC ;

JOBLIN, KN ;

PRESTON, AF .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (03) :583-&

[6] 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

[7]

de Pascual-Teresa T., 1985, TETRAHEDRON LETT, V26, P5717

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

DECORZANT, R ;

VIAL, C ;

NAF, F ;

WHITESIDES, GM .

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

[9]

GONZALEZSIERRA M, 1987, HETEROCYCLES, V26, P2801

[10] ODEUR ET CONSTITUTION .4. SUR LES EPOXYDES HYDROAROMATIQUES A ODEUR AMBREE [J].

HINDER, M ;

STOLL, M .

HELVETICA CHIMICA ACTA, 1950, 33 (05) :1308-1312

← 1 2 →