HIGHLY CONVERGENT ENANTIOSELECTIVE ROUTE TO TRICHOTHECENES

被引：13

作者：

GILBERT, JC

SELLIAH, RD

机构：

[1] Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 42期

关键词：

TRICHOTHECENES; ENANTIOSELECTIVE SYNTHESIS; ESTER ENOLATE REARRANGEMENT;

D O I：

10.1016/S0040-4039(00)60947-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of (+)-15-hydroxytrichothec-9,12-diene (4) has been accomplished in 16 steps and in 5.5% overall yield from the optically active beta-hydroxyester 9. Creation of the vicinal quaternary centers resulted from a highly enantio- and diastereoselective Ireland-Claisen ester-enolate rearrangement.

引用

页码：6259 / 6262

页数：4

共 16 条

[1] MYCOTOXINS FROM FUSARIUM SPECIES - DETECTION, DETERMINATION AND VARIETY
APSIMON, JW
BLACKWELL, BA
BLAIS, L
FIELDER, DA
GREENHALGH, R
KASITU, G
MILLER, JD
SAVARD, M
[J]. PURE AND APPLIED CHEMISTRY, 1990, 62 (07) : 1339 - 1346
[2] TOTAL SYNTHESIS OF THE TRICHOTHECENE MYCO-TOXIN ANGUIDINE
BROOKS, DW
GROTHAUS, PG
MAZDIYASNI, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) : 4472 - 4473
[3] THE STEREOSELECTIVITY OF THE ALKYLATION OF THE DIANION OF ETHYL 2-HYDROXY-6-METHYLCYCLOHEXANECARBOXYLATES - CONTROL OF STEREOCHEMISTRY AT 3 ADJACENT STEREOGENIC CENTERS
FRATER, G
GUNTHER, W
MULLER, U
[J]. HELVETICA CHIMICA ACTA, 1989, 72 (08) : 1846 - 1851
[4] GILBERT JA, UNPUB
[5] MODEL STUDIES FOR THE SYNTHESIS OF TRICHOTHECENES - SYNTHESIS OF RAC-TRICHODIENE AND RAC-BAZZANENE
GILBERT, JC
WIECHMAN, BE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (02) : 258 - 260
[6] THE NMR-SPECTRA OF TRICHOTHECENES AND RELATED FUNGAL METABOLITES
GREENHALGH, R
BLACKWELL, BA
SAVARD, ME
[J]. TETRAHEDRON, 1989, 45 (08) : 2373 - 2383
[7] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-12,13-EPOXYTRICHOTHEC-9-ENE AND ITS ANTIPODE
HUA, DH
VENKATARAMAN, S
CHANYUKING, R
PAUKSTELIS, JV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4741 - 4748
[8] THE CONVERGENT SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS - THE SYNTHESIS OF THE MONENSIN BIS(TETRAHYDROFURAN) VIA THE CLAISEN REARRANGEMENT OF AN ESTER ENOLATE WITH A BETA-LEAVING GROUP
IRELAND, RE
NORBECK, DW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) : 3279 - 3285
[9] ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION
IRELAND, RE
MUELLER, RH
WILLARD, AK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) : 2868 - 2877
[10] JANSSEN CGM, 1982, SYNTHESIS-STUTTGART, P389

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