Synthesis of a broad array of highly functionalized, enantiomerically pure cyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions

被引：72

作者：

Myers, AG ^{[1
]}

Siegel, DR ^{[1
]}

Buzard, DJ ^{[1
]}

Charest, MG ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 18期

关键词：

D O I：

10.1021/ol010151m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We have found that the 1,2-dihydroxylation of benzoic acid with Alcaligenes eutrophus strain B9, first reported in 1971 by Reiner and Hegeman, is readily adapted for the preparation of tens to hundreds of grams of (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid of > 95% ee. This unique substrate undergoes many specific oxidative and rearrangement processes. Among these are transformations of unanticipated chemical novelty and many products that have not been previously described.

引用

页码：2923 / 2926

页数：4

共 22 条

[1] A BIOTECH ROUTE TO POLYPHENYLENE [J].

BALLARD, DGH ;

COURTIS, A ;

SHIRLEY, IM ;

TAYLOR, SC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :954-955

[2] BETA-LACTONE FORMATION IN A HALOGENO-LACTONIZATION REACTION [J].

BARNETT, WE ;

MCKENNA, JC .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (11) :551-&

[3] THE USE OF CYCLOHEXA-3,5-DIENE-1,2-DIOLS IN ENANTIOSPECIFIC SYNTHESIS [J].

CARLESS, HAJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :795-826

[4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[5] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[6]

DITRICH K, 1990, LIEBIGS ANN CHEM, P15

[7] OXIDATIVE DEGRADATION OF AROMATIC HYDROCARBONS BY MICROORGANISMS .2. METABOLISM OF HALOGENATED AROMATIC HYDROCARBONS [J].

GIBSON, DT ;

KOCH, JR ;

SCHULD, CL ;

KALLIO, RE .

BIOCHEMISTRY, 1968, 7 (11) :3795-&

[8] MICROBIAL OXIDATION OF AROMATICS IN ENANTIOCONTROLLED SYNTHESIS .2. RATIONAL DESIGN OF AZA SUGARS (ENDO-NITROGENOUS) - TOTAL SYNTHESIS OF (+)-KIFUNENSINE, MANNOJIRIMYCIN, AND OTHER GLYCOSIDASE INHIBITORS [J].

HUDLICKY, T ;

ROUDEN, J ;

LUNA, H ;

ALLEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5099-5107

[9] A SHORT SYNTHESIS OF (+)-LYCORICIDINE [J].

HUDLICKY, T ;

OLIVO, HF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9694-9696

[10] Toluene dioxygenase-mediated cis-dihydroxylation of aromatics in enantioselective synthesis. Asymmetric total syntheses of pancratistatin and 7-deoxypancratistatin, promising antitumor agents [J].

Hudlicky, T ;

Tian, XR ;

Konigsberger, K ;

Maurya, R ;

Rouden, J ;

Fan, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10752-10765

← 1 2 3 →