Toward an efficient synthesis of taxane analogs by dienyne ring-closing metathesis

被引：28

作者：

Aldegunde, Maria J. ^{[1
]}

Castedo, Luis ^{[1
]}

Granja, Juan R. ^{[1
]}

机构：

[1] Univ Santiago, Dept Quim Organ, Fac Quim, Labs CSIC, Santiago De Compostela 15782, Spain

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 17期

关键词：

D O I：

10.1021/ol801469h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient tandem ring-closing dienyne metathesis of dienynes derived from cyclohex-2-enone affords the [5.3.1] carbon framework characteristic of taxanes in a single-step process. Further stereoselective functionalizations of the resulting [5.3.1] carbon framework lead to an advanced intermediate in a novel synthetic strategy for taxane analogs.

引用

页码：3789 / 3792

页数：4

共 57 条

[1] Dienyne ring-closing metathesis approach for the construction of taxosteroids [J].

Aldegunde, Maria J. ;

Garcia-Fandino, Rebeca ;

Castedo, Luis ;

Granja, Juan R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5135-5150

[2]

[Anonymous], 2003, HDB METATHESIS

[3]

[Anonymous], 2004, MODERN ALDOL REACTIO

[4]

[Anonymous], 2004, MODERN ALDOL REACTIO

[5] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[6]

Bourgeois D, 2000, ANGEW CHEM INT EDIT, V39, P725, DOI 10.1002/(SICI)1521-3773(20000218)39:4<725::AID-ANIE725>3.3.CO

[7]

2-9

[8] RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].

BUNCE, RA .

TETRAHEDRON, 1995, 51 (48) :13103-13159

[9] An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin [J].

Crimmins, MT ;

Choy, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5653-5660

[10] The taxanes: an update [J].

Crown, J ;

O'Leary, M .

LANCET, 2000, 355 (9210) :1176-1178

← 1 2 3 4 5 6 →