Synthesis of a C4-epi-C1-C6 fragment of FR901464 using a novel bromolactolization

被引：27

作者：

Albert, BJ ^{[1
]}

Koide, K ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol049160w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of a C4-epi-C1-C6 fragment of the antitumor agent FR901464 is reported. The advanced intermediate prepared in this study contains two of the three correct stereocenters found in the C1-C6 moiety of FR901464. For the preparation of this intermediate, we have developed a highly diastereoselective bromolactolization of a delta-alkenyl ketone.

引用

收藏

页码：3655 / 3658

页数：4

相关论文

共 20 条

[1]

[Anonymous], CATALYTIC ASYMMETRIC

[2]

ARLUENGA J, 2003, J AM CHEM SOC, V125, P9028

[3] Asymmetric induction of the lodolactonization reaction of α-sulfurated γ-unsaturated amides [J].

Blot, V ;

Reboul, V ;

Metzner, P .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1196-1201

[4] INVESTIGATION OF THE EARLY STAGES OF ELECTROPHILIC ADDITION OF BR2 TO OLEFINS - KINETIC EVIDENCE FOR A REVERSIBLY FORMED BROMONIUM ION IN THE REACTION OF BR2 WITH TETRAISOBUTYLETHYLENE [J].

BROWN, RS ;

SLEBOCKATILK, H ;

BENNET, AJ ;

BELLUCCI, G ;

BIANCHINI, R ;

AMBROSETTI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6310-6316

[5] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[6] Transcription factors as targets for cancer therapy [J].

Darnell, JE .

NATURE REVIEWS CANCER, 2002, 2 (10) :740-749

[7] 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

[8]

Dossetter AG, 1999, ANGEW CHEM INT EDIT, V38, P2398, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2398::AID-ANIE2398>3.0.CO

[9]

2-E

[10] Promising new developments in cancer chemotherapy [J].

Ferrante, K ;

Winograd, B ;

Canetta, R .

CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1999, 43 (Suppl 1) :S61-S68