Interrupting the nazarov cyclization with indoles

被引：40

作者：

Basak, Ashok K. ^{[1
]}

Tius, Marcus A. ^{[1
,2
]}

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 18期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/ol801587u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A carbon-terminated interrupted Nazarov reaction is described. The trimethylsilyl enol ethers derived from propargyl vinyl ketones undergo selective proton transfer at the distal acetylenic carbon atom to provide allenyl vinyl ketones as transient intermediates. In the presence of indoles, a cascade of reactions is initiated that converts the initially formed pentadienyl cations to cyclopentenones bearing a quaternary alpha carbon atom.

引用

页码：4073 / 4076

页数：4

共 35 条

[1] Total synthesis of (±)-terpestacin and (±)-11-epi-terpestacin
Berger, Gideon O.
Tius, Marcus A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) : 6473 - 6480
[2] Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization -: electrophilic aromatic substitution
Browder, CC
Marmsäter, FP
West, FG
[J]. CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (02) : 375 - 385
[3] Highly efficient trapping of the Nazarov intermediate with substituted arenes
Browder, CC
Marmsäter, FP
West, FG
[J]. ORGANIC LETTERS, 2001, 3 (19) : 3033 - 3035
[4] Interrupted nazarov cyclization on silica gel
Dhoro, F
Tius, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) : 12472 - 12473
[5] The Nazarov cyclization in organic synthesis. Recent advances
Frontier, AJ
Collison, C
[J]. TETRAHEDRON, 2005, 61 (32) : 7577 - 7606
[6] Unexpected participation of an unconjugated olefin during Nazarov cyclization of bridged bicyclic dienones
Giese, S
Mazzola, RD
Amann, CM
Arif, AM
West, FG
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) : 6546 - 6549
[7] Ionic hydrogenation of oxyallyl intermediates: the reductive Nazarov cyclization
Giese, S
West, FG
[J]. TETRAHEDRON, 2000, 56 (52) : 10221 - 10228
[8] Giese S, 2000, ANGEW CHEM INT EDIT, V39, P1970, DOI 10.1002/1521-3773(20000602)39:11<1970::AID-ANIE1970>3.0.CO
[9] 2-B
[10] Interrupted nazarov reactions using dichlorocyclopropanes: A novel mode of arene trapping
Grant, Tina N.
West, F. G.
[J]. ORGANIC LETTERS, 2007, 9 (19) : 3789 - 3792

← 1 2 3 4 →