Total synthesis of (±)-merrilactone A

被引：71

作者：

Mehta, G ^{[1
]}

Singh, SR ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 06期

关键词：

diastereoselectivity; natural products; neurotrophic agents; terpenoids; total synthesis;

D O I：

10.1002/anie.200503618

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Merrily, merrily: A total synthesis of the pentacyclic sesquiterpenoid mercilactone A starting from 2,3-dimethyl-2- cyclopentene-1,4-dione has been achieved with good stereo- and regioselectivity. Merrilactone A exhibits impressive neurotrophic activity and may be important for the development of therapeutic drugs for neurodegenerative disorders. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：953 / 955

页数：3

共 16 条

[1] The total synthesis of (±)-merrilactone A [J].

Birman, VB ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2080-2081

[2]

Danishefsky S.J., 2005, ANGEW CHEM, V117, P1535, DOI DOI 10.1002/ANGE.200462509

[3] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[4] Synthetic studies toward merrilactone A: a short synthesis of AB ring motif [J].

Harada, K ;

Kato, H ;

Fukuyama, Y .

TETRAHEDRON LETTERS, 2005, 46 (43) :7407-7410

[5] Pharmacology of neurotrophic factors [J].

Hefti, F .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1997, 37 :239-267

[6] Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum [J].

Huang, JM ;

Yokoyama, R ;

Yang, CS ;

Fukuyama, Y .

TETRAHEDRON LETTERS, 2000, 41 (32) :6111-6114

[7] Structures of merrilactones B and C, novel anislactone-type sesquiterpenes from Illicium merrillianum, and chemical conversion of anislactone B to merrilactone A [J].

Huang, JM ;

Yang, CS ;

Tanaka, M ;

Fukuyama, Y .

TETRAHEDRON, 2001, 57 (22) :4691-4698

[8] Structure and neurotrophic activity of seco-prezizaane-type sesquiterpenes from Illicium merrillianum [J].

Huang, JM ;

Yokoyama, R ;

Yang, CS ;

Fukuyama, Y .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (04) :428-431

[9] Total synthesis of merrilactone A [J].

Inoue, M ;

Sato, T ;

Hirama, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10772-10773

[10] A Paterno-Buchi approach to the synthesis of merrilactone A [J].

Iriondo-Alberdi, J ;

Perea-Buceta, JE ;

Greaney, MF .

ORGANIC LETTERS, 2005, 7 (18) :3969-3971

← 1 2 →