The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol

被引：8

作者：

Burckhardt, S ^{[1
]}

Ley, SV ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 07期

关键词：

D O I：

10.1039/b201164f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of the natural products alpha- and beta-zearalenol 1 and 2 has been achieved using pi -allyltricarbonyliron lactone complexes to control the 1,5-stereochemical relationship of the oxygen functionalities found in these resorcylic macrolides.

引用

页码：874 / 882

页数：9

共 31 条

[1]

BETINA V, 1989, MYCOTOXINS CHEM BIOL, P271

[2]

CARUSO M, 1990, SYNLETT, P224

[3] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].

COREY, EJ ;

NICOLAOU, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616

[4] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[5] Total syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands [J].

Fürstner, A ;

Thiel, OR ;

Kindler, N ;

Bartkowska, B .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7990-7995

[6] VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].

GAO, Y ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539

[7] ALKYLATION OF DIANION OF BETA-KETO PHOSPHONATES - VERSATILE SYNTHESIS OF DIMETHYL (2-OXOALKYL)PHOSPHONATES [J].

GRIECO, PA ;

POGONOWSKI, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (09) :3071-3072

[8] IDENTIFICATION OF THE NATURALLY OCCURRING ISOMER OF ZEARALENOL PRODUCED BY FUSARIUM-ROSEUM GIBBOSUM IN RICE CULTURE [J].

HAGLER, WM ;

MIROCHA, CJ ;

PATHRE, SV ;

BEHRENS, JC .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1979, 37 (05) :849-853

[9] TOTAL SYNTHESIS OF THE MYCOTOXIN (-)-ZEARALENONE BASED ON MACROCYCLIZATION USING A CINNAMYL RADICAL INTERMEDIATE [J].

HITCHCOCK, SA ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11) :1323-1328

[10] Improved Cr(II)-mediated synthesis of E-alkenyl-stannanes from aldehydes using Bu3SnCHI2 in DMF [J].

Hodgson, DM ;

Foley, AM ;

Lovell, PJ .

TETRAHEDRON LETTERS, 1998, 39 (35) :6419-6420

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