SYNTHETIC APPLICATIONS OF GROUP-IV METAL IMIDO COMPLEX-ALKYNE [2+2] CYCLOADDITIONS - A CONCISE TOTAL SYNTHESIS OF (+/-)-MONOMORINE

被引:116
作者
MCGRANE, PL [1 ]
LIVINGHOUSE, T [1 ]
机构
[1] MONTANA STATE UNIV,DEPT CHEM & BIOCHEM,BOZEMAN,MT 59717
关键词
D O I
10.1021/jo00031a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Monocyclopentadienyltitanium(IV) imido complexes readily undergo [2 + 2] cycloadditions with representative alkynes at less-than-or-equal-to 25-degrees-C. The present study details the application of a catalytic variation of this reaction in a convergent synthesis of (+/-)-monomorine.
引用
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页码:1323 / 1324
页数:2
相关论文
共 38 条
[32]   SYNTHESIS OF (+/-)-PHYLLANTHOCIN VIA A METAL-CATALYZED CYCLOREDUCTION [J].
TROST, BM ;
EDSTROM, ED .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :520-522
[33]   SYNTHESIS OF 1-HYDROXY-2-THIOURACIL [J].
WARRENER, RN ;
CAIN, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (05) :511-&
[34]   TOTAL SYNTHESIS OF (+/-)-DIHYDROPINIDINE, (+/-)-MONOMORINE-I, AND (+/-)-INDOLIZIDINE-223AB (GEPHYROTOXIN-223AB) BY INTRAMOLECULAR NITROSO DIELS-ALDER REACTION [J].
WATANABE, Y ;
IIDA, H ;
KIBAYASHI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4088-4097
[35]   NICKEL-CATALYZED INTRAMOLECULAR [4 + 4] CYCLO-ADDITIONS .4. ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-ASTERISCANOLIDE [J].
WENDER, PA ;
IHLE, NC ;
CORREIA, CRD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5904-5906
[36]   AN ORGANOCHROMIUM-MEDIATED SYNTHESIS OF 11-DEOXYDAUNOMYCINONE VIA A TANDEM BENZANNULATION/FRIEDEL-CRAFTS DOUBLE CYCLIZATION [J].
WULFF, WD ;
XU, YC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2312-2314
[37]   AN EFFICIENT REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (+/-)-MONOMORINE-I VIA THE HIGHLY REGIOSELECTIVE ALPHA-ALKYNYLATION OF A 1-ACYLPYRIDINIUM SALT [J].
YAMAGUCHI, R ;
HATA, E ;
MATSUKI, T ;
KAWANISI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :2094-2096
[38]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-MONOMORINE-I [J].
YAMAZAKI, N ;
KIBAYASHI, C .
TETRAHEDRON LETTERS, 1988, 29 (45) :5767-5768