CHEMOENZYMATIC APPROACH TO THE AB RING-SYSTEM OF AKLAVINONE

被引：26

作者：

GUANTI, G ^{[1
]}

BANFI, L ^{[1
]}

BRUSCO, S ^{[1
]}

RIVA, R ^{[1
]}

机构：

[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFAT & AROMAT,I-16132 GENOA,ITALY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)61382-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of compound 3, a possible intermediate for the AB ring system 2 of Aklavinone 1, were obtained in optically active form from diol 7. Key steps were the preparation of both enantiomers of monoacetate 8d, via enzymatic reactions that utilize PPL as catalyst, and the construction of ring A in a totally regioselective manner.

引用

页码：8549 / 8552

页数：4

共 17 条

[1] CHEMOENZYMATIC PREPARATION OF A KEY INTERMEDIATE FOR CARBAPENEM SYNTHESIS STARTING FROM ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-ASTERISK) [J].

BANFI, L ;

GUANTI, G ;

NARISANO, E .

TETRAHEDRON, 1993, 49 (33) :7385-7392

[2] SELECTIVE CLEAVAGE OF THE ALLYL AND ALLYLOXCARBONYL GROUPS THROUGH PALLADIUM-CATALYZED HYDROSTANNOLYSIS WITH TRIBUTYLTIN HYDRIDE - APPLICATION TO THE SELECTIVE PROTECTION-DEPROTECTION OF AMINO-ACID DERIVATIVES AND IN PEPTIDE-SYNTHESIS [J].

DANGLES, O ;

GUIBE, F ;

BALAVOINE, G ;

LAVIELLE, S ;

MARQUET, A .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4984-4993

[3] ASYMMETRIC-SYNTHESIS OF THE AB-RING OF AKLAVINONE [J].

DAVIS, FA ;

KUMAR, A .

TETRAHEDRON LETTERS, 1991, 32 (52) :7671-7674

[4] A USEFUL APPLICATION OF BENZYL TRICHLOROACETIMIDATE FOR THE BENZYLATION OF ALCOHOLS [J].

ECKENBERG, P ;

GROTH, U ;

HUHN, T ;

RICHTER, N ;

SCHMECK, C .

TETRAHEDRON, 1993, 49 (08) :1619-1624

[5] HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP [J].

FUJI, K ;

ICHIKAWA, K ;

NODE, M ;

FUJITA, E .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1661-1664

[6] SYNTHESIS OF MOSESIN-4, A NATURALLY-OCCURRING STEROID SAPONIN WITH SHARK REPELLENT ACTIVITY, AND ITS ANALOG 7-BETA-GALACTOSYL ETHYL CHOLATE [J].

GARGIULO, D ;

BLIZZARD, TA ;

NAKANISHI, K .

TETRAHEDRON, 1989, 45 (17) :5423-5432

[7]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[8] TANDEM REDUCTION INTRAMOLECULAR HYDROXYALKYLATION OF (3-HYDROXYPHENYL)ALKANOATES - A NEW REGIOSELECTIVE APPROACH TO 1,8-DIHYDROXYTETRALINS [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E ;

RIVA, R ;

THEA, S .

TETRAHEDRON LETTERS, 1992, 33 (27) :3919-3922

[9] ENZYME CATALYZED MONOHYDROLYSIS OF 2-ARYL-1,3-PROPANEDIOL DIACETATES - A STUDY OF STRUCTURAL EFFECTS OF THE ARYL MOIETY ON THE ENANTIOSELECTIVITY [J].

GUANTI, G ;

NARISANO, E ;

PODGORSKI, T ;

THEA, S ;

WILLIAMS, A .

TETRAHEDRON, 1990, 46 (20) :7081-7092

[10]

GUANTI G, UNPUB TETRAHEDRON AS

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