New approach to bicyclo[5.3.0]decanes:: Stereoselective guaiane synthesis

被引：29

作者：

Coquerel, Y ^{[1
]}

Greene, AE ^{[1
]}

Deprés, JP ^{[1
]}

机构：

[1] Univ Grenoble 1, LEDSS, F-38041 Grenoble, France

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

关键词：

D O I：

10.1021/ol035763g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A conceptually new and highly versatile approach to bicyclo[5.3.0]decanes, based on dichloroketene cycloaddition-diazoalkane ring expansion, is disclosed, and its relevance to natural product synthesis is demonstrated through the preparation of three guaiane sesquiterpenes. A concise total synthesis of a guaian-8,12-olide, 6-deoxygeigerin, highlights the effectiveness of the new methodology.

引用

收藏

页码：4453 / 4455

页数：3

相关论文

共 29 条

[21] SYNTHESIS AND STEREOCHEMISTRY OF 5-SUBSTITUTED 2-METHYLCYCLOHEPTANONES [J].

MARSHALL, JA ;

PARTRIDGE, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4090-+

[22] An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate [J].

Procopiou, PA ;

Baugh, SPD ;

Flack, SS ;

Inglis, GGA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2342-2347

[23] A new guaiane type sesquiterpene from Torilis japonica [J].

Ryu, JH ;

Jeong, YS .

ARCHIVES OF PHARMACAL RESEARCH, 2001, 24 (06) :532-535

[24]

Trost BM, 2001, ANGEW CHEM INT EDIT, V40, P2313, DOI 10.1002/1521-3773(20010618)40:12<2313::AID-ANIE2313>3.0.CO

[25]

2-H

[26] THERMODYNAMIC RESULTS FOR GEOMETRICAL ISOMERISM IN SILYL KETENE ACETALS [J].

WILCOX, CS ;

BABSTON, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (08) :1451-1453

[27] The first total synthesis of (±)-ingenol [J].

Winkler, JD ;

Rouse, MB ;

Greaney, MF ;

Harrison, SJ ;

Jeon, YT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9726-9728

[28]

Yokoyama R, 2001, J CHEM SOC PERK T 1, P2257, DOI 10.1039/b104164a

[29] SESQUITERPENE LACTONES AND OTHER TERPENES FROM GEIGERIA SPECIES [J].

ZDERO, C ;

BOHLMANN, F .

PHYTOCHEMISTRY, 1989, 28 (11) :3105-3120