Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A1

被引：17

作者：

Debnar, Thomas ^{[1
]}

Wang, Tongtong ^{[1
]}

Menche, Dirk ^{[1
]}

机构：

[1] Univ Bonn, Kekule Intitute Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

关键词：

METAL-PROMOTED CYCLIZATION; ENANTIOSELECTIVE SYNTHESIS; ABSOLUTE-CONFIGURATION; CARBONYL METHYLENATION; ROUTE; HYDROGENATION; ASSIGNMENT; REAGENTS; ALKYNES; ENYNES;

D O I：

10.1021/ol401110x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.

引用

页码：2774 / 2777

页数：4

共 42 条

[1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[2] A new ligand class for the asymmetric dihydroxylation of olefins [J].

Becker, H ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451

[3] Unusual biosynthesis of leupyrrins in the myxobacterium Sorangium cellulosum [J].

Bode, HB ;

Wenzel, SC ;

Irschik, H ;

Höfle, G ;

Müller, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (32) :4163-4167

[4] IMPROVED PROCEDURE FOR THE ASYMMETRIC REDUCTION OF PROCHIRAL KETONES BY B-(3-PINANYL)-9-BORABICYCLO[3.3.1]NONANE [J].

BROWN, HC ;

PAI, GG .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) :1606-1608

[5]

Burk MJ, 1998, ANGEW CHEM INT EDIT, V37, P1931, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1931::AID-ANIE1931>3.0.CO

[6]

2-3

[7] AN ENOLATE CLAISEN ROUTE TO C-PYRANOSIDES - DEVELOPMENT AND APPLICATION TO AN IONOPHORE SYNTHON [J].

BURKE, SD ;

ARMISTEAD, DM ;

SCHOENEN, FJ ;

FEVIG, JM .

TETRAHEDRON, 1986, 42 (11) :2787-2801

[8] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[9] Highly regioselective opening of zirconacyclopentadienes by remote coordination: concise synthesis of the furan core of the leupyrrins [J].

Debnar, Thomas ;

Dreisigacker, Sandra ;

Menche, Dirk .

CHEMICAL COMMUNICATIONS, 2013, 49 (07) :725-727

[10] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

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