Total synthesis of eupomatilones 4 and 6: Structurally rearranged and atropisomerically fluxional lignan natural products

被引：41

作者：

Coleman, RS ^{[1
]}

Gurrala, SR ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 22期

关键词：

D O I：

10.1021/ol048333e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent and diastereocontrolled total synthesis of eupomatilones 4 and 6 is reported and was based on a diastereoselective hydroboration/oxidation sequence and a convergent Lipshutz biarylcuprate cross-coupling reaction. The structure of eupomatilone 6 is revised.

引用

收藏

页码：4025 / 4028

页数：4

相关论文

共 25 条

[1] Total synthesis of attenols A and B [J].

Araki, K ;

Suenaga, K ;

Sengoku, T ;

Uemura, D .

TETRAHEDRON, 2002, 58 (10) :1983-1995

[2] INDIUM IN ORGANIC-SYNTHESIS - INDIUM-MEDIATED ALLYLATION OF CARBONYL-COMPOUNDS [J].

ARAKI, S ;

ITO, H ;

BUTSUGAN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1831-1833

[3] A sultone approach to the C(1)-C(18) moiety of pamamycin-607 [J].

Bernsmann, H ;

Fröhlich, R ;

Metz, P .

TETRAHEDRON LETTERS, 2000, 41 (22) :4347-4351

[4] SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - SECONDARY ORBITAL EFFECTS INVOLVING D-PI-P-PI INTERACTIONS [J].

BURGESS, K ;

CASSIDY, J ;

OHLMEYER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1020-1027

[5] CONSTITUENTS OF EUPOMATIA SPECIES .14. THE STRUCTURES OF EUPOMATILONE-1, EUPOMATILONE-2, EUPOMATILONE-3, EUPOMATILONE-4, EUPOMATILONE-5, EUPOMATILONE-6 AND EUPOMATILONE-7 ISOLATED FROM EUPOMATIA-BENNETTII [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (12) :1705-1714

[6] CONSTITUENTS OF EUPOMATIA SPECIES .12. ISOLATION OF CONSTITUENTS OF THE TUBERS AND AERIAL PARTS OF EUPOMATIA-BENNETTII AND DETERMINATION OF THE STRUCTURES OF NEW ALKALOIDS FROM THE AERIAL PARTS OF E-BENNETTII AND MINOR ALKALOIDS OF E-LAURINA [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (11) :1615-1626

[7] ATROPDIASTEREOSELECTIVE TOTAL SYNTHESIS OF PHLEICHROME AND THE PROTEIN-KINASE-C INHIBITOR CALPHOSTIN-A [J].

COLEMAN, RS ;

GRANT, EB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8795-8796

[8]

COLEMAN RS, UNPUB

[9]

COUTTS LD, 1993, SYNLETT, P696

[10] EFFECT OF THE ACIDIC COMPONENT ON THE MITSUNOBU INVERSION OF A STERICALLY HINDERED ALCOHOL [J].

DODGE, JA ;

TRUJILLO, JI ;

PRESNELL, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :234-236