SYNTHESIS OF (+)-VERNOLEPIN RELATED-COMPOUNDS FROM GERMACRANOLIDES

被引:11
作者
BARRERO, AF
OLTRA, JE
BARRAGAN, A
机构
[1] Dto. de Química Orgánica, Facultad de Ciencias, 18071 Granada, Campus Fuentenueva s/n
关键词
D O I
10.1016/0040-4039(94)02238-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+)-8-O-acetyl-1,2,11,13-tetrahydro-8-epi -vernolepin (11) was synthesized from salonitenolide (4). The key steps were the Cope rearrangement of the germacradiene skeleton to elemadiene and the long-range functionalization at C-14, which allows the intramolecular cyclisation necessary for the formation of the delta-lactone ring of 11.
引用
收藏
页码:311 / 314
页数:4
相关论文
共 18 条
  • [1] SYNTHESIS OF TERPENOID COMPOUNDS FROM ALPHA-SANTONIN
    BANERJEE, AK
    VERA, WJ
    GONZALEZ, NC
    [J]. TETRAHEDRON, 1993, 49 (22) : 4761 - 4788
  • [2] BARRERO AF, IN RPESS FITOTERAPIA
  • [3] INTRAMOLECULAR HYDROGEN ABSTRACTION - IODOSOBENZENE DIACETATE, AN EFFICIENT AND CONVENIENT REAGENT FOR ALKOXY RADICAL GENERATION
    CONCEPCION, JI
    FRANCISCO, CG
    HERNANDEZ, R
    SALAZAR, JA
    SUAREZ, E
    [J]. TETRAHEDRON LETTERS, 1984, 25 (18) : 1953 - 1956
  • [4] CONNOLLY JD, 1991, DICT TERPENOIDS, V1, P231
  • [5] (+/-)-DEOXYVERNOLEPIN - CYTOTOXIC VERNOLEPIN PROTOTYPE
    GRIECO, PA
    NOGUEZ, JA
    MASAKI, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (03) : 495 - 502
  • [6] HEATHCOCK CH, 1983, TOTAL SYNTHESIS NATU, V5, P93
  • [7] SYNTHESIS OF (+)-8-DEOXYVERNOLEPIN
    HERNANDEZ, R
    RODRIGUEZ, MS
    VELAZQUEZ, SM
    SUAREZ, E
    [J]. TETRAHEDRON LETTERS, 1993, 34 (25) : 4105 - 4108
  • [8] THE USE OF 4,4-DISUBSTITUTED NOPINONES FOR NATURAL-PRODUCT SYNTHESIS - SYNTHESIS OF ELEMANOID SESQUITERPENES
    KATO, M
    WATANABE, M
    VOGLER, B
    AWEN, BZ
    MASUDA, Y
    TOOYAMA, Y
    YOSHIKOSHI, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 7071 - 7076
  • [9] PREPARATION OF KEY INTERMEDIATES FOR THE ASYMMETRIC-SYNTHESIS OF OXYGENATED ELEMANOIDS
    KATO, M
    KIDO, F
    WATANABE, M
    MASUDA, Y
    AWEN, BZ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (22): : 2831 - 2836
  • [10] EFFICIENT PREPARATION OF A KEY INTERMEDIATE SUITABLE FOR THE ASYMMETRIC-SYNTHESIS OF (+)-VERNOLEPIN AND (-)-VERNOMENIN
    KATO, M
    KIDO, F
    MASUDA, Y
    WATANABE, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (09) : 697 - 698