MICHAEL INITIATED RING-CLOSURE REACTIONS IN NATURAL PRODUCT SYNTHESIS - A CONCISE ENTRY TO THE PODOPHYLLINS

被引:21
|
作者
HARROWVEN, DC
机构
[1] Department of Chemistry, University of Wales, Bangor
关键词
D O I
10.1016/S0040-4020(01)91221-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid entry towards the Podophyllum lignans is described exemplified by a concise regioselective total synthesis of taiwanin E 5 and chinensinaphthol 6. The approach features a Michael Initiated Ring Closure (MIRC type II) sequence to access the key lignan intermediates IIa & b from the ketodithianes 10a & b and 2-(5H)-furanone.
引用
收藏
页码:9039 / 9048
页数:10
相关论文
共 50 条
  • [41] 5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE
    BALDWIN, JE
    CUTTING, J
    DUPONT, W
    KRUSE, L
    SILBERMAN, L
    THOMAS, RC
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 736 - 738
  • [42] SOLVENT EFFECTS ON RING-CLOSURE REACTIONS OF ENZYMATIC MODEL COMPOUNDS
    KOSHLAND, DE
    DAFFORN, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1975, 170 (AUG24): : 38 - 38
  • [43] ACID-CATALYZED RING-CLOSURE REACTIONS OF ELECTROPHILIC ALKENES
    VERHE, R
    DEKIMPE, N
    COURTHEYN, D
    DEBUYCK, L
    SCHAMP, N
    TETRAHEDRON, 1982, 38 (24) : 3649 - 3660
  • [44] ACID-CATALYZED RING-CLOSURE REACTIONS OF ELECTROPHILIC ALKENES
    VERHE, R
    DEKIMPE, N
    DEBUYCK, L
    COURTHEYN, D
    SCHAMP, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 251 - ORGN
  • [45] CYCLOADDITION REACTIONS OF PHENYLALLENE - RING-CLOSURE OF THE DIRADICAL INTERMEDIATE INVOLVING THE AROMATIC RING
    PASTO, DJ
    YANG, SH
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) : 1676 - 1680
  • [46] Unveiling the beauty of cyclopropane formation: a comprehensive survey of enantioselective Michael initiated ring closure (MIRC) reactions
    Moorthy, Ramkumar
    Bio-Sawe, Waidath
    Thorat, Sagar S.
    Sibi, Mukund P.
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4560 - 4601
  • [47] PYRIDINE RING-CLOSURE IN SYNTHESIS OF QUINOLINES ACCORDING COMBES
    YAMASHKIN, SA
    YUDIN, LG
    KOST, AN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1992, (08): : 1011 - 1024
  • [48] On-Surface Synthesis of Non-Benzenoid Nanographenes by Oxidative Ring-Closure and Ring-Rearrangement Reactions
    Lohr, Thorsten G.
    Urgel, Jose, I
    Eimre, Kristjan
    Liu, Junzhi
    Di Giovannantonio, Marco
    Mishra, Shantanu
    Berger, Reinhard
    Ruffieux, Pascal
    Pignedoli, Carlo A.
    Fasel, Roman
    Feng, Xinliang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (31) : 13565 - 13572
  • [49] AN EASY ENTRY TO ISOQUINOLINE ALKALOIDS BY AZA-WITTIG ELECTROCYCLIC RING-CLOSURE
    RODRIGUES, JAR
    LEIVA, GC
    DESOUSA, JDF
    TETRAHEDRON LETTERS, 1995, 36 (01) : 59 - 62
  • [50] ELECTROCYCLIC RING-CLOSURE OF [2.2.6]PARACYCLOPHANEPENTAENE - STRUCTURE AND DYNAMIC STEREOCHEMISTRY OF THE PRODUCT
    TANNER, D
    WENNERSTROM, O
    OLSSON, T
    TETRAHEDRON LETTERS, 1983, 24 (48) : 5407 - 5410