The synthesis of (-)-Ambrox® starting from labdanolic acid

被引:35
作者
Bolster, MG [1 ]
Jansen, BJM [1 ]
de Groot, A [1 ]
机构
[1] Univ Wageningen & Res Ctr, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands
关键词
Ambrox((R)); labdanolic acid; iododecarboxylation;
D O I
10.1016/S0040-4020(01)00493-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iododecarboxylation of labdanolic acid (1), followed by dehydrohalogenation led to alkenes 4 and 12. Both compounds were converted into (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydro-2-naphthalenol (8), which was transformed via cyclization into (-)-Ambrox((R)) (9). (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5657 / 5662
页数:6
相关论文
共 36 条
[1]  
[Anonymous], SYNTHETIC REAGENTS
[2]   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
[3]   SYNTHESIS OF AMBROX(R) FROM COMMUNIC ACIDS [J].
BARRERO, AF ;
ALTAREJOS, J ;
ALVAREZMANZANEDA, EJ ;
RAMOS, JM ;
SALIDO, S .
TETRAHEDRON, 1993, 49 (28) :6251-6262
[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 DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTHO[2,1-B]FURAN VIA ALKOXY RADICAL FRAGMENTATION [J].
CHRISTENSON, PA .
TETRAHEDRON, 1988, 44 (07) :1925-1932
[7]   IODOSOBENZENE DIACETATE, AN EFFICIENT REAGENT FOR THE OXIDATIVE DECARBOXYLATION OF CARBOXYLIC-ACIDS [J].
CONCEPCION, JI ;
FRANCISCO, CG ;
FREIRE, R ;
HERNANDEZ, R ;
SALAZAR, JA ;
SUAREZ, E .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (03) :402-404
[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]   SYNTHESIS OF 3-BETA-HYDROXY[21-C-14]-5-BETA-PREGN-8(14)-EN-20-ONE FROM CHENODEOXYCHOLIC ACID [J].
DELUCA, ME ;
SELDES, AM ;
GROS, EG .
HELVETICA CHIMICA ACTA, 1986, 69 (08) :1844-1850