Total syntheses of neuroprotective mastigophorenes A and B

被引：42

作者：

Fukuyama, Y ^{[1
]}

Matsumoto, K

Tonoi, Y

Yokoyama, R

Takahashi, H

Minami, H

Okazaki, H

Mitsumoto, Y

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Inst Pharmacognosy, Tokushima 7708514, Japan

[2] Otsuka Pharmaceut Co Ltd, Tokushima New Drug Res Inst, Tokushima 7710192, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 33期

关键词：

mastigophorene; herbertane-type sesquiterpene; Heck reaction; horseradish peroxidase; neuroprotective activity;

D O I：

10.1016/S0040-4020(01)00631-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Herbertenediol (3) which is regarded as a biosynthetic precursor of mastigophorenes A and B has been effectively synthesized from (R)-1,2-dimethyl-2-cyclopentene carboxylic acid by applying an intramolecular Heck reaction to the construction of the quaternary carbon center, and then horseradish peroxidase-catalyzed oxidative coupling of 3 has given rise to (-)-mastigophorenes A and B. Mastigophorenes A and B have been found to exhibit significant neuroprotective activity in primary cultures of fetal rat cortical neurons. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7127 / 7135

页数：9

共 16 条

[1] EFFECTS OF RECOMBINANT HUMAN BASIC FIBROBLAST GROWTH-FACTOR AND ITS MODIFIED PROTEIN CS23 ON SURVIVAL OF PRIMARY CULTURED NEURONS FROM VARIOUS REGIONS OF FETAL-RAT BRAIN [J].

ABE, K ;

TAKAYANAGI, M ;

SAITO, H .

JAPANESE JOURNAL OF PHARMACOLOGY, 1990, 53 (02) :221-227

[2] STEREOSELECTIVE REACTIONS .21. ASYMMETRIC ALKYLATION OF ALPHA ALKYL BETA-KETO-ESTERS TO ALPHA,ALPHA-DIALKYL BETA-KETO-ESTERS HAVING EITHER (R)-CHIRAL OR (S)-CHIRAL QUATERNARY CENTER DEPENDING ON THE SOLVENT SYSTEM [J].

ANDO, K ;

TAKEMASA, Y ;

TOMIOKA, K ;

KOGA, K .

TETRAHEDRON, 1993, 49 (08) :1579-1588

[3] Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B [J].

Bringmann, G ;

Pabst, T ;

Henschel, P ;

Kraus, J ;

Peters, K ;

Peters, EM ;

Rycroft, DS ;

Connolly, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9127-9133

[4] Novel concepts in directed biaryl synthesis - Part 76 - First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol [J].

Bringmann, G ;

Pabst, T ;

Rycroft, DS ;

Connolly, JD .

TETRAHEDRON LETTERS, 1999, 40 (03) :483-486

[5] Atropo-enantioselective synthesis of a simplified analog of mastigophorenes A and B [J].

Bringmann, G ;

Pabst, T ;

Busemann, S ;

Peters, K ;

Peters, EM .

TETRAHEDRON, 1998, 54 (08) :1425-1438

[6]

CHAU P, 1987, Proceedings of the National Science Council Republic of China Part A Physical Science and Engineering, V11, P124

[7] ENANTIOSELECTIVE SYNTHESIS OF 2-METHYL-2-HYDROXY-GAMMA-BUTYROLACTONE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF FRONTALIN AND MEVALONOLACTONE [J].

DAVIS, FA ;

REDDY, GV ;

CHEN, BC ;

KUMAR, A ;

HAQUE, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6148-6153

[8] Total syntheses of (-)-herbertenediol, (-)-mastigophorene A, and (-)-mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines [J].

Degnan, AP ;

Meyers, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) :2762-2769

[9] MASTIGOPHORENES - NOVEL DIMERIC ISOCUPARANE-TYPE SESQUITERPENOIDS FROM THE LIVERWORT MASTIGOPHORA-DICLADOS [J].

FUKUYAMA, Y ;

TOYOTA, M ;

ASAKAWA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (19) :1341-1342

[10] Total synthesis of herbertenediol, an isocuparane sesquiterpene isolated from liverworts [J].

Fukuyama, Y ;

Kiriyama, Y ;

Kodama, M .

TETRAHEDRON LETTERS, 1996, 37 (08) :1261-1264

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