A new example of 1α-hydroxylation of drimanic terpenes through combined microbial and chemical processes

被引：20

作者：

Aranda, G

Moreno, L

Cortés, M

Prangé, T

Maurs, M

Azerad, R

机构：

[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, UMR 8601, F-75270 Paris 06, France

[2] Ecole Polytech, UMR 7652, Organ Synth Lab, F-91128 Palaiseau, France

[3] Pontificia Univ Catolica Chile, Fac Quim, Santiago, Chile

[4] UFR Biomed, UPRESA 7031, F-93017 Bobigny, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 28期

关键词：

confertifolin; biotransformation; microbial hydroxylation; functionalization transfer;

D O I：

10.1016/S0040-4020(01)00595-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Among various filamentous fungi, Aspergillus niger ATCC 9142 was the most efficient strain to convert confertifolin in high yield into its 3 beta -hydroxy derivative, which was then chemically converted to 1 alpha -hydroxy-, 1 alpha ,11 alpha -dihydroxy- and 1 alpha -acetoxy-11 alpha -hydroxyconfertifolin, new compounds structurally related to bioactive natural products isolated from plants or marine sponges. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6051 / 6056

页数：6

相关论文

共 20 条

[1] SESQUITERPENOIDS .2. THE CONSTITUTION AND STEREOCHEMISTRY OF DRIMENIN, ISODRIMENIN, AND CONFERTIFOLIN [J].

APPEL, HH ;

CONNOLLY, JD ;

OVERTON, KH ;

BOND, RPM .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (NOV) :4685-4692

[2] SESQUITERPENOIDS .3. CONSTITUTION AND STEREOCHEMISTRY OF VALDIVIOLIDE, FUEGIN, WINTERIN AND FUTRONOLIDE [J].

APPEL, HH ;

BOND, RPM ;

OVERTON, KH .

TETRAHEDRON, 1963, 19 (04) :635-&

[3] Functionalization of natural drimanic compounds via microbial/chemical tandem reactions [J].

Aranda, G ;

Bertranne-Delahaye, M ;

Lallemand, JY ;

Azerad, R ;

Maurs, M ;

Cortes, M ;

Lopez, J .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 5 (1-4) :203-206

[4] 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

[5] 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

[6] 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

[7] 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

[8] MICROBIAL TRANSFORMATIONS OF 7-ALPHA-HYDROXYFRULLANOLIDE [J].

ATTAURRAHMAN ;

CHOUDHARY, MI ;

ATA, A ;

ALAM, M ;

FAROOQ, A ;

PERVEEN, S ;

SHEKHANI, MS ;

AHMED, N .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1251-1255

[9]

AZERAD R, 2000, STEREOSELECTIVE BIOC, P153, DOI DOI 10.1201/9781420027242.CH6

[10] SCALARIN, A NEW PENTACYCLIC C-25 TERPENOID FROM SPONGE CACOSPONGIA-SCALARIS [J].

FATTORUSSO, E ;

MAGNO, S ;

SANTACROCE, C ;

SICA, D .

TETRAHEDRON, 1972, 28 (24) :5993-5997