OXIDATION AND ELIMINATION-REACTIONS STUDY IN A FORMAL SYNTHESIS OF (+/-)-FORSKOLIN

被引:11
作者
ANIES, C [1 ]
PANCRAZI, A [1 ]
LALLEMAND, JY [1 ]
机构
[1] ECOLE POLYTECH,DCSO,CNRS,ORGAN SYNTH LAB,F-91128 PALAISEAU,FRANCE
关键词
FORMAL SYNTHESIS; FORSKOLIN; OXIDATION; ELIMINATION REACTION;
D O I
10.1016/0040-4039(95)00223-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
From the dihydrofuran derivative 3, an mCPBA oxidation followed by an LAH reduction led to the 9 beta-hydroxy lactol 11, the Jones' oxidation of which gave the 9 beta-hydroxy lactone 13 together with the formyl ketone compound 7. Treatment of 13 with SOCl(2-)Py finally produced the Ziegler-Corey-Ikegami intermediate lactone 2 leading to a formal synthesis of (+/-)-forskoline.
引用
收藏
页码:2075 / 2078
页数:4
相关论文
共 32 条
  • [1] ANIES C, 1994, TETRAHEDRON LETT, V35, P7771
  • [2] SULFURANES .6. REACTIONS INVOLVING ALKOXY LIGANDS OF DIALKOXYDIARYLSULFURANES - FORMATION OF OLEFINS AND ETHERS
    ARHART, RJ
    MARTIN, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) : 5003 - &
  • [3] BHAT SV, 1977, TETRAHEDRON LETT, P1669, DOI 10.1016/S0040-4039(01)93245-9
  • [4] REACTIONS OF FORSKOLIN, A BIOLOGICALLY-ACTIVE DITERPENOID FROM COLEUS-FORSKOHLII
    BHAT, SV
    BAJWA, BS
    DORNAUER, H
    DESOUZA, NJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03): : 767 - 771
  • [5] 1,4-DIOXENE IN ORGANIC-SYNTHESIS - AN APPROACH TO THE A,B RING-SYSTEM OF FORSKOLIN
    BLANCHOTCOURTOIS, V
    FETIZON, M
    HANNA, I
    [J]. TETRAHEDRON LETTERS, 1992, 33 (35) : 5061 - 5064
  • [6] AN UNUSUAL BASE INDUCED 1,5-ELECTROCYCLIZATION OF A TETRACYCLIC 1,4-CYCLOHEXADIENE DERIVATIVE
    BLANCHOTCOURTOIS, V
    HANNA, I
    PRANGE, T
    [J]. TETRAHEDRON LETTERS, 1992, 33 (35) : 5065 - 5066
  • [7] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS
    BURGESS, EM
    PENTON, HR
    TAYLOR, EA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 26 - 31
  • [8] THE PATHOGENESIS AND MEDICAL-MANAGEMENT OF GLAUCOMA
    CAPRIOLI, J
    [J]. DRUG DEVELOPMENT RESEARCH, 1985, 6 (03) : 193 - 215
  • [9] SYNTHETIC ROUTES TO FORSKOLIN
    COLOMBO, MI
    ZINCZUK, J
    RUVEDA, EA
    [J]. TETRAHEDRON, 1992, 48 (06) : 963 - 1037
  • [10] SYNTHESIS OF THE ZIEGLER KEY INTERMEDIATE AND RELATED PRECURSORS FOR THE SYNTHESIS OF FORSKOLIN AND ERIGEROL
    COLOMBO, MI
    ZINCZUK, J
    BACIGALUPPO, JA
    SOMOZA, C
    RUVEDA, EA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) : 5631 - 5639