Total Synthesis of (-)-Isoschizogamine

被引：48

作者：

Miura, Yusuke ^{[1
]}

Hayashi, Noriyuki ^{[1
]}

Yokoshima, Satoshi ^{[1
]}

Fukuyama, Tohru ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 29期

基金：

日本学术振兴会;

关键词：

AUS SCHIZOZYGIA CAFFAEOIDES; 1,4-DIPOLAR CYCLOADDITION; ORGANIC-SYNTHESIS; ISOSCHIZOGAMINE; METATHESIS; EFFICIENT; REAGENTS; (+/-)-ISOSCHIZOGAMINE; EXPLORATIONS; CATALYSTS;

D O I：

10.1021/ja305856q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A first asymmetric total synthesis of (-)-isoschizogamine has been accomplished. Our synthesis features the facile construction of the carbon framework of the natural product through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereo-selective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

引用

页码：11995 / 11997

页数：3

共 20 条

[1] VINYL-LITHIUM REAGENTS FROM ARENESULFONYLHYDRAZONES [J].

CHAMBERLIN, AR ;

STEMKE, JE ;

BOND, FT .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :147-154

[2] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[3] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[4]

GERTEISEN TJ, 1971, J ORG CHEM, V36, P3255

[5] Revised structure of isoschizogamine [J].

Hájícek, J ;

Taimr, J ;

BudÄsínsky, M .

TETRAHEDRON LETTERS, 1998, 39 (5-6) :505-508

[6] A ring-rearrangement metathesis approach toward the synthesis of cyclopenta- and cyclohexa[c]indene systems [J].

Holtsclaw, J ;

Koreeda, M .

ORGANIC LETTERS, 2004, 6 (21) :3719-3722

[7] Total synthesis of (±)-isoschizogamine [J].

Hubbs, JL ;

Heathcock, CH .

ORGANIC LETTERS, 1999, 1 (08) :1315-1317

[8] Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds:: Large accelerating effects of bases and ligands [J].

Itooka, R ;

Iguchi, Y ;

Miyaura, N .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) :6000-6004

[9]

LEY SV, 1994, SYNTHESIS-STUTTGART, P639

[10] Efficient construction of cyclopenta[b]quinoline core of isoschizozygane alkaloids via intramolecular formal hetero-Diels-Alder reaction [J].

Magomedov, NA .

ORGANIC LETTERS, 2003, 5 (14) :2509-2512

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