Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors

被引：105

作者：

Banwell, MG ^{[1
]}

Edwards, AJ ^{[1
]}

Harfoot, GJ ^{[1
]}

Jolliffe, KA ^{[1
]}

McLeod, MD ^{[1
]}

McRae, KJ ^{[1
]}

Stewart, SG ^{[1
]}

Vögtle, M ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

PURE AND APPLIED CHEMISTRY | 2003年 / 75卷 / 2-3期

关键词：

D O I：

10.1351/pac200375020223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.

引用

页码：223 / 229

页数：7

共 34 条

[1] ENANTIOSELECTIVE BACTERIAL BIOTRANSFORMATION ROUTES TO CIS-DIOL METABOLITES OF MONOSUBSTITUTED BENZENES, NAPHTHALENE AND BENZOCYCLOALKENES OF EITHER ABSOLUTE-CONFIGURATION [J].

ALLEN, CCR ;

BOYD, DR ;

DALTON, H ;

SHARMA, ND ;

BRANNIGAN, I ;

KERLEY, NA ;

SHELDRAKE, GN ;

TAYLOR, SC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :117-118

[2] ISOLATION AND STRUCTURE ELUCIDATION OF TSUGICOLINES A-D NOVEL PROTOILLUDANE SESQUITERPENES FROM LAURILIA-TSUGICOLA [J].

ARNONE, A ;

BRAMBILLA, U ;

NASINI, G ;

DEPAVA, OV .

TETRAHEDRON, 1995, 51 (48) :13357-13364

[3] Chemoenzymatic total synthesis of the sesquiterpene (-)-patchoulenone [J].

Banwell, M ;

McLeod, M .

CHEMICAL COMMUNICATIONS, 1998, (17) :1851-1852

[4] First total synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) from a non-carbohydrate source [J].

Banwell, M ;

De Savi, C ;

Watson, K .

CHEMICAL COMMUNICATIONS, 1998, (11) :1189-1190

[5]

Banwell M. G., UNPUB

[6] Chemoenzymatic synthesis of (+)-aspicilin from chlorobenzene [J].

Banwell, MG ;

McRae, KJ .

ORGANIC LETTERS, 2000, 2 (23) :3583-3586

[7] A SHORT, REGIOCONTROLLED TOTAL SYNTHESIS OF THE MOLD METABOLITE STIPITATIC ACID [J].

BANWELL, MG ;

DUPUCHE, JR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (02) :203-207

[8] A chemoenzymatic synthesis of differentially protected D-talose derivatives [J].

Banwell, MG ;

Edwards, AJ ;

Lambert, JN ;

Ma, XH ;

Watson, KG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2002, 55 (1-2) :95-103

[9] Chemoenzymatic total syntheses of the sesquiterpene (-)-patchoulenone [J].

Banwell, MG ;

Hockless, DCR ;

McLeod, MD .

NEW JOURNAL OF CHEMISTRY, 2003, 27 (01) :50-59

[10] A chemoenzymatic synthesis of the 12-membered macrolide (-)-cladospolide A [J].

Banwell, MG ;

Jolliffe, KA ;

Loong, DTJ ;

McRae, KJ ;

Vounatsos, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, Royal Society of Chemistry (01) :22-25

← 1 2 3 4 →