REMARKABLE STEREOCHEMICAL INVERSION IN SOME HECK ARYLATION REACTIONS - A MECHANISTIC PROPOSAL

被引：13

作者：

MCCLURE, KF ^{[1
]}

DANISHEFSKY, SJ ^{[1
]}

SCHULTE, GK ^{[1
]}

机构：

[1] YALE UNIV,CTR CHEM INSTRUMENTAT,NEW HAVEN,CT 06511

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 02期

关键词：

D O I：

10.1021/jo00081a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Internal arylation reactions of enol ethers were used to form the 1,5-epoxybenzazocine ring system of FR 900482. An interesting inversion process was observed for Z-enol ethers.

引用

页码：355 / 360

页数：6

共 18 条

[1] THE MICHAELIS-ARBUZOV REARRANGEMENT [J].

BHATTACHARYA, AK ;

THYAGARAJAN, G .

CHEMICAL REVIEWS, 1981, 81 (04) :415-430

[2] A NEW APPROACH TO THE BICYCLIC HYDROXYLAMINE HEMIKETAL RING-SYSTEM OF ANTITUMOR-ANTIBIOTIC FR900482 VIA OXIDATIVE RING EXPANSION OF A TETRAHYDROPYRROLO[1,2-A]INDOLE [J].

DMITRIENKO, GI ;

DENHART, D ;

MITHANI, S ;

PRASAD, GKB ;

TAYLOR, NJ .

TETRAHEDRON LETTERS, 1992, 33 (39) :5705-5708

[3]

DOYLE DG, 1989, CHEM REV, V89, P1433

[4] TOTAL SYNTHESIS OF (+/-)-FR-900482 [J].

FUKUYAMA, T ;

XU, LH ;

GOTO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :383-385

[5]

GOTO S, 1989, TETRAHEDRON LETT, V30, P6491

[6]

Heck R.F., 1985, PALLADIUM REAGENTS O

[7] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .19 TAXONOMIC STUDIES ON THE PRODUCING STRAIN - A NEW SPECIES OF THE GENUS STREPTOMYCES [J].

IWAMI, M ;

KIYOTO, S ;

TERANO, H ;

KOHSAKA, M ;

AOKI, H ;

IMANAKA, H .

JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :589-593

[8] ENANTIOSPECIFIC SYNTHESIS OF AN AZIRIDINOBENZOAZOCINONE, AN ADVANCED INTERMEDIATE CONTAINING THE CORE NUCLEUS OF FR900482 AND FK973 [J].

JONES, RJ ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1144-1146

[9] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .2. PRODUCTION, ISOLATION, CHARACTERIZATION AND BIOLOGICAL-ACTIVITY [J].

KIYOTO, S ;

SHIBATA, T ;

YAMASHITA, M ;

KOMORI, T ;

OKUHARA, M ;

TERANO, H ;

KOHSAKA, M ;

AOKI, H ;

IMANAKA, H .

JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :594-599

[10] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

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