First enantioselective total synthesis of (-)-heliannuol C

被引：52

作者：

Kamei, T ^{[1
]}

Shindo, M ^{[1
]}

Shishido, K ^{[1
]}

机构：

[1] Univ Tokushima, Inst Med Resources, Tokushima 7708505, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 46期

关键词：

lipase; ring-closing metathesis; diastereoselective epoxidation; cleavage of epoxide; sesquiterpene;

D O I：

10.1016/j.tetlet.2003.09.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first, efficient total synthesis of (-)-heliannuol C (1) was accomplished enantioselectively, using a chemoenzymatic desymmetrization of the 6-symmetrical diol, a ring closing metathesis, a diastereoselective epoxidation, and a regioselective reductive cleavage of epoxide as the key reaction steps. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8505 / 8507

页数：3

共 10 条

[1] Enantioselective synthesis of heliannuol E; Structural consideration of natural molecule [J].

Doi, F ;

Ogamino, T ;

Sugai, T ;

Nishiyama, S .

TETRAHEDRON LETTERS, 2003, 44 (26) :4877-4880

[2] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

[3]

Kaiho T., 1994, [No title captured], Patent No. [JP 6,128,238, 6128238, JP 06128238, 06128238]

[4] Enantioselective total synthesis of (-)-heliannuol A [J].

Kishuku, H ;

Shindo, M ;

Shishido, K .

CHEMICAL COMMUNICATIONS, 2003, (03) :350-351

[5] STRUCTURAL ELUCIDATION AND CHEMISTRY OF A NOVEL FAMILY OF BIOACTIVE SESQUITERPENES - HELIANNUOLS [J].

MACIAS, FA ;

MOLINILLO, JMG ;

VARELA, RM ;

TORRES, A ;

FRONCZEK, FR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8261-8266

[6] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[7] Total synthesis of (-)-heliannuol E [J].

Sato, K ;

Yoshimura, T ;

Shindo, M ;

Shishido, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :309-314

[8] Enantioselective total synthesis of heliannuols D and A [J].

Takabatake, K ;

Nishi, I ;

Shindo, M ;

Shishido, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1807-1808

[9] The development of L2X2Ru=CHR olefin metathesis catalysts:: An organometallic success story [J].

Trnka, TM ;

Grubbs, RH .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (01) :18-29

[10] EPOXIDATION OF OLEFINS USING METHYL(TRIFLUOROMETHYL)DIOXIRANE GENERATED IN-SITU [J].

YANG, D ;

WONG, MK ;

YIP, YC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3887-3889

← 1 →