FORMAL 2+2 AND 3+2 CYCLOADDITION REACTIONS OF 2H-CHROMENES WITH 2-ALKOXY-1,4-BENZOQUINONES - REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED PTEROCARPANS

被引:73
作者
ENGLER, TA
REDDY, JP
COMBRINK, KD
VANDERVELDE, D
机构
[1] Department of Chemistry, University of Kansas, Lawrence
关键词
D O I
10.1021/jo00291a027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The titanium(IV)-catalyzed reaction of various 2H-chromenes and 2-alkoxy-l,4-benzoquinones stereoselectively yields the oxygenated pterocarpans 8 and/or the 2 + 2 adducts 7, depending upon reaction conditions. Cyclobutanes 7 rearrange to 8 upon treatment with protic acids. Syntheses of the pterocarpan phytoalexins (±)-homopterocarpin (2), (±)-pterocarpin (3), and (±)-9-0-benzy1-3-0-methylsophoropterocarpan A (4) are presented, which demonstrates the synthetic utility of these formal cycloaddition reactions. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:1248 / 1254
页数:7
相关论文
共 50 条
[41]   REACTIONS OF PHOSPHORUS COMPUNDS .15. A GENERAL SYNTHESIS OF 2H-1BENZOPYRANS [J].
SCHWEIZE.EE ;
LIEHR, J ;
MONACO, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2416-&
[42]   PREPARATION OF ORGANOLITHIUM COMPOUNDS BY TRANSMETALATION REACTION .3. ALLYLLITHIUM AND METHALLYLLITHIUM [J].
SEYFERTH, D ;
WEINER, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (12) :4797-&
[43]   STRUCTURE ACTIVITY RELATIONSHIP OF SOME BEAN PHYTOALEXINS AND RELATED ISOFLAVONOIDS [J].
STOSSEL, P .
PHYSIOLOGICAL PLANT PATHOLOGY, 1985, 26 (03) :269-277
[44]   SAUERSTOFF-HETERORINGE - DIE KONFIGURATION UND SYNTHESE DES D,L-HOMOPTEROCARPINS [J].
SUGINOME, H ;
IWADARE, T .
EXPERIENTIA, 1962, 18 (04) :163-&
[45]   OXYGEN HETEROCYCLES - MAACKIAIN, A NEW NATURALLY OCCURRING CHROMANOCOUMARAN [J].
SUGINOME, H .
EXPERIENTIA, 1962, 18 (04) :161-&
[46]   SOME OBSERVATIONS ON PHOTOLYSIS OF FUSED CYCLOPENTYL NITRITIES [J].
SUGINOME, H ;
SATO, N ;
MASAMUNE, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1969, 42 (01) :215-+
[47]   REACTIONS OF METAL SALTS WITH MELTED LIGANDS - A CONVENIENT METHOD FOR PREPARATION OF COMPLEXES WITH SOME GROUP VA DONORS [J].
TAYIM, HA ;
BOULDOUK.A ;
AWAD, F .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1970, 32 (12) :3799-&
[48]  
TOMITA M, 1968, CHEM PHARM BULL, V16, P523
[49]   HOST-PATHOGEN INTERACTIONS .23. THE MECHANISM OF THE ANTI-BACTERIAL ACTION OF GLYCINOL, A PTEROCARPAN PHYTOALEXIN SYNTHESIZED BY SOYBEANS [J].
WEINSTEIN, LI ;
ALBERSHEIM, P .
PLANT PHYSIOLOGY, 1983, 72 (02) :557-563
[50]   OXIDATIONS WITH POTASSIUM NITROSODISULFONATE (FREMYS RADICAL - TEUBER REACTION [J].
ZIMMER, H ;
LANKIN, DC ;
HORGAN, SW .
CHEMICAL REVIEWS, 1971, 71 (02) :229-&