An approach to the synthesis of phomactins using a Wittig rearrangement

被引:4
|
作者
Marsden, A [1 ]
Thomas, EJ [1 ]
机构
[1] Univ Manchester, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
关键词
2,3-Wittig rearrangement; phomactins; propargylic ether;
D O I
10.3998/ark.5550190.0003.909
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preliminary studies to evaluate the feasability of an approach to the synthesis of the phomactin diterpenes are outlined. The key step is the 2,3-Wittig rearrangement of the propargylic ether 32 which gives a mixture of the diastereoisomeric alcohols 33. Oxidation to the ketones 34 and 35 followed by conjugate addition of lithium dimethylcuprate and deprotection gives the unsaturated diketone 37 so providing a strategy for the synthesis of the cyclohexenyl core of the phomactins.
引用
收藏
页码:78 / 92
页数:15
相关论文
共 50 条
  • [21] WITTIG REARRANGEMENT OF (DIARYLMETHOXY)ACETAMIDES
    VANDERSTELT, C
    HEUS, WJ
    HAASJES, A
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1973, 92 (04): : 493 - 512
  • [22] WITTIG REARRANGEMENT OF SOME THIACYCLOPHANES
    MITCHELL, RH
    OTSUBO, T
    BOEKELHEIDE, V
    TETRAHEDRON LETTERS, 1975, (03) : 219 - 222
  • [23] THE IMINO-WITTIG REARRANGEMENT
    KATRITZKY, AR
    PONKSHE, NK
    TETRAHEDRON LETTERS, 1981, 22 (13) : 1215 - 1216
  • [24] The aza-Wittig rearrangement
    Vogel, C
    SYNTHESIS-STUTTGART, 1997, (05): : 497 - &
  • [25] Synthesis of unit A of cryptophycin via a [2,3]-Wittig rearrangement
    Liang, J
    Hoard, DW
    Van Khau, V
    Martinelli, MJ
    Moher, ED
    Moore, RE
    Tius, MA
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1459 - 1463
  • [26] Studies on Wittig rearrangement of furfuryl ethers in steroidal side chain synthesis
    Tsubuki, M
    Ohinata, A
    Tanaka, T
    Takahashi, K
    Honda, T
    TETRAHEDRON, 2005, 61 (05) : 1095 - 1100
  • [27] SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT
    BOL, KM
    LISKAMP, RMJ
    TETRAHEDRON LETTERS, 1991, 32 (39) : 5401 - 5404
  • [28] SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT
    BOL, KM
    LISKAMP, RMJ
    TETRAHEDRON, 1992, 48 (31) : 6425 - 6438
  • [29] Synthesis of unit A of cryptophycin via a [2,3]-Wittig rearrangement
    Liang, Jian
    Hoard, David W.
    Van, Khau, Vien
    Martinelli, Michael J.
    Moher, Eric D.
    Moore, Richard E.
    Tius, Marcus A.
    Journal of Organic Chemistry, 1999, 64 (2-5): : 1459 - 1463
  • [30] SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES
    COLDHAM, I
    COLLIS, AJ
    MOULD, RJ
    RATHMELL, RE
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (21): : 2739 - 2745