Functionalization of natural drimanic compounds via microbial/chemical tandem reactions

被引:7
作者
Aranda, G [1 ]
Bertranne-Delahaye, M
Lallemand, JY
Azerad, R
Maurs, M
Cortes, M
Lopez, J
机构
[1] Ecole Polytech, Synth Organ Lab, URA 1308 CNRS, F-91128 Palaiseau, France
[2] Univ Paris 05, URA 400 CNRS, Chim & Biochim Pharmacol & Toxicol Lab, F-75006 Paris, France
[3] Pontificia Univ Catolica Chile, Fac Quim, Santiago, Chile
关键词
terpenes; 3; beta-hydroxylation; 1; alpha-hydroxylation; polygodial; cinnamodial; warburganal; forskolin; scalaradial; Aspergillus niger;
D O I
10.1016/S1381-1177(98)00035-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The direct microbial 3 beta-hydroxylation of drimanic terpenes by filamentous fungi, followed by a transfer of the functionalization from the 3 beta- to the 1 alpha-position has been used for preparing derivatives of antifeedant terpenic compounds bearing an additional 1 alpha-hydroxyl group. The semisynthesis of 1 alpha-hydroxypolygodial is described as an example. (C) 1998 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:203 / 206
页数:4
相关论文
共 16 条
[1]   Practical and efficient 1 alpha-hydroxylation of 4,4-dimethyl-2-ene derivatives in terpenic series. [J].
Aranda, G ;
BertranneDelahaye, M ;
Azerad, R ;
Maurs, M ;
Cortes, M ;
Ramirez, H ;
Vernal, G ;
Prange, T .
SYNTHETIC COMMUNICATIONS, 1997, 27 (01) :45-60
[2]   NEW APPLICATION OF THE MITSUNOBU REACTION FOR THE PREPARATION OF (DELTA-2) DERIVATIVES IN TERPENIC SERIES [J].
ARANDA, G ;
LALLEMAND, JY ;
AZERAD, R ;
MAURS, M ;
CORTES, M ;
RAMIREZ, H ;
VERNAL, G .
SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2525-2535
[3]   MICROBIAL TRANSFORMATION OF DITERPENES - HYDROXYLATION OF SCLAREOL, MANOOL AND DERIVATIVES BY MUCOR-PLUMBEUS [J].
ARANDA, G ;
ELKORTBI, MS ;
LALLEMAND, JY ;
NEUMAN, A ;
HAMMOUMI, A ;
FACON, I ;
AZERAD, R .
TETRAHEDRON, 1991, 47 (39) :8339-8350
[4]   MICROBIOLOGICAL HYDROXYLATION IN THE DRIMANE SERIES [J].
ARANDA, G ;
FACON, I ;
LALLEMAND, JY ;
LECLAIRE, M ;
AZERAD, R ;
CORTES, M ;
LOPEZ, J ;
RAMIREZ, H .
TETRAHEDRON LETTERS, 1992, 33 (51) :7845-7848
[5]   MICROBIAL HYDROXYLATION OF SCLAREOL BY MUCOR-PLUMBEUS [J].
ARANDA, G ;
LALLEMAND, JY ;
HAMMOUMI, A ;
AZERAD, R .
TETRAHEDRON LETTERS, 1991, 32 (15) :1783-1786
[6]   STRUCTURE OF POLYGODIAL - A NEW SESQUITERPENE DIALDEHYDE FROM POLYGONUM HYDROPIPER L [J].
BARNES, CS ;
LODER, JW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1962, 15 (02) :322-&
[7]  
BARUAH RN, 1994, CHEM IND, P975
[8]   DRIMENDIOL, A SESQUITERPENE FROM DRYMIS-WINTERII [J].
BROWN, GD .
PHYTOCHEMISTRY, 1994, 35 (04) :975-977
[9]   SESQUITERPENOIDS OF CINNAMOSMA FRAGRANS BAILLON - STRUCTURE OF CINNAMOLIDE, CINNAMOSMOLIDE AND CINNAMODIAL [J].
CANONICA, L ;
CORBELLA, A ;
GARIBOLDI, P ;
JOMMI, G ;
KREPINSKY, J ;
FERRARI, G ;
CASAGRAN.C .
TETRAHEDRON, 1969, 25 (17) :3895-+
[10]   SYNTHETIC ROUTES TO FORSKOLIN [J].
COLOMBO, MI ;
ZINCZUK, J ;
RUVEDA, EA .
TETRAHEDRON, 1992, 48 (06) :963-1037