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
ABE, K
TAKAYANAGI, M
SAITO, H
[J]. 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
ANDO, K
TAKEMASA, Y
TOMIOKA, K
KOGA, K
[J]. 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
Bringmann, G
Pabst, T
Henschel, P
Kraus, J
Peters, K
Peters, EM
Rycroft, DS
Connolly, JD
[J]. 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
Bringmann, G
Pabst, T
Rycroft, DS
Connolly, JD
[J]. TETRAHEDRON LETTERS, 1999, 40 (03) : 483 - 486
[5] Atropo-enantioselective synthesis of a simplified analog of mastigophorenes A and B
Bringmann, G
Pabst, T
Busemann, S
Peters, K
Peters, EM
[J]. 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
DAVIS, FA
REDDY, GV
CHEN, BC
KUMAR, A
HAQUE, MS
[J]. 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
Degnan, AP
Meyers, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) : 2762 - 2769
[9] MASTIGOPHORENES - NOVEL DIMERIC ISOCUPARANE-TYPE SESQUITERPENOIDS FROM THE LIVERWORT MASTIGOPHORA-DICLADOS
FUKUYAMA, Y
TOYOTA, M
ASAKAWA, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (19) : 1341 - 1342
[10] Total synthesis of herbertenediol, an isocuparane sesquiterpene isolated from liverworts
Fukuyama, Y
Kiriyama, Y
Kodama, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (08) : 1261 - 1264

← 1 2 →