SYNTHESIS AND REACTIONS OF ENEDIYNES AND ENYNE-ALLENES

被引：1

作者：

WANG, KK

机构：

[1] Department of Chemistry, West Virginia University, Morgantown, West Virginia

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 1995年 / 42卷 / 04期

关键词：

ENEDIYNES; ENYNE-ALLENES; CARBON BIRADICALS; O-QUINODIMETHANES;

D O I：

10.1002/jccs.199500099

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The thermal cycloaromatization reactions of (Z)-3-hexene-1,5-diynes (enediynes) and (Z)-1,2,4-heptatrien-6-ynes (enyne-allenes) provide easy entries to a variety of carbon biradicals. Several new synthetic routes to these highly unsaturated compounds were developed by using multifunctional reagents properly substituted with combinations of boron, silicon, and tin appendages. Condensation of gamma-(trialkylsilyl)allenylboranes 1 and 2 with conjugated acetylenic and allenic aldehydes followed by the elimination step of the Peterson olefination reaction furnished enediynes and enyne-allenes with high geometric purity. Convenient procedures for the synthesis of enediynes and enyne-allenes were also developed by using alkenylboronic ester 28 and the trimethyltin-substituted alkenylboranes 34 for cross-coupling reactions. On heating, acyclic enyne-allene 22 underwent a sequence of intramolecular transformations through biradical intermediates to form 26, providing a new example of a one-step 0 --> ABCD ring construction of the tetracyclic steroidal skeleton.

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页码：745 / 749

页数：5

相关论文

共 56 条

[41] MOLECULAR DESIGN, CHEMICAL SYNTHESIS, AND BIOLOGICAL ACTION OF ENEDIYNES [J].

NICOLAOU, KC ;

SMITH, AL .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :497-503

[42]

OPPOLZER W, 1978, SYNTHESIS-STUTTGART, P793

[43] INTERACTION OF CALICHEAMICIN WITH DUPLEX DNA - ROLE OF THE OLIGOSACCHARIDE DOMAIN AND IDENTIFICATION OF MULTIPLE BINDING MODES [J].

PALOMA, LG ;

SMITH, JA ;

CHAZIN, WJ ;

NICOLAOU, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) :3697-3708

[44] TRANSANNULAR DIELS-ALDER ROUTE TO SYSTEMS RELATED TO DYNEMICIN-A [J].

PORCO, JA ;

SCHOENEN, FJ ;

STOUT, TJ ;

CLARDY, J ;

SCHREIBER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7410-7411

[45] SYNTHESIS AND CRYSTALLOGRAPHIC ANALYSIS OF A BICYCLIC CORE RELATED TO THE ESPERAMICIN-CALICHEMICIN AGLYCONES [J].

SCHOENEN, FJ ;

PORCO, JA ;

SCHREIBER, SL ;

VANDUYNE, GD ;

CLARDY, J .

TETRAHEDRON LETTERS, 1989, 30 (29) :3765-3768

[46] ISOLATION, STRUCTURE DETERMINATION, AND PROPOSED MECHANISM OF ACTION FOR ARTIFACTS OF MADUROPEPTIN CHROMOPHORE [J].

SCHROEDER, DR ;

COLSON, KL ;

KLOHR, SE ;

ZEIN, N ;

LANGLEY, DR ;

LEE, MS ;

MATSON, JA ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9351-9352

[47] THE ENOL-KETO TRIGGER IN INITIATING ARENE DIRADICAL FORMATION IN CALICHEAMICIN ESPERAMICIN ANALOGS [J].

SEMMELHACK, MF ;

GALLAGHER, JJ ;

MINAMI, T ;

DATE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11618-11619

[48] PREPARATION OF (Z)-ALKENES, KETONES, AND ALKYNES VIA TRIALKYLTIN CHLORIDE INDUCED INTRAMOLECULAR TRANSFER-REACTION OF LITHIUM 1-ALKYNYLTRIALKYLBORATES - STEREOSELECTIVE SYNTHESIS OF THE SEX-PHEROMONES OF THE DOUGLAS-FIR TUSSOCK MOTH, THE GYPSY-MOTH, AND THE WILD SILKMOTH ANTHERAEA-POLYPHEMUS [J].

WANG, KK ;

CHU, KH .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5175-5178

[49] A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF ENYNE-ALLENES [J].

WANG, KK ;

WANG, ZG .

TETRAHEDRON LETTERS, 1994, 35 (12) :1829-1832

[50] STEREOSELECTIVE SYNTHESIS OF ENEDIYNES AND ENYNES BY CONDENSATION OF ALDEHYDES WITH GAMMA-(TRIALKYLSILYL)ALLENYLBORANES [J].

WANG, KK ;

WANG, ZG ;

GU, YG .

TETRAHEDRON LETTERS, 1993, 34 (52) :8391-8394

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