PYRANOSE ALPHA-ENONES PROVIDE READY ACCESS TO FUNCTIONALIZED TRANS-DECALINS VIA BIS-ANNULATED PYRANOSIDES OBTAINED BY INTRAMOLECULAR DIELS-ALDER REACTIONS - A KEY INTERMEDIATE FOR FORSKOLIN

被引:39
作者
TSANG, R [1 ]
FRASERREID, B [1 ]
机构
[1] DUKE UNIV,DEPT CHEM,PAUL M GROSS CHEM LAB,DURHAM,NC 27706
关键词
D O I
10.1021/jo00030a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular Diels-Alder routes for the preparation of bis-annulated pyranosides, as chiral precursors of functionalized trans-decalin rings of terpenoid natural products, have been investigated.
引用
收藏
页码:1065 / 1067
页数:3
相关论文
共 26 条
  • [1] CONJUGATE ADDITION OF METHANOL TO ALPHA-ENONES - PHOTOCHEMISTRY AND STEREOCHEMICAL DETAILS
    BENKO, Z
    FRASERREID, B
    MARIANO, PS
    BECKWITH, ALJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) : 2066 - 2072
  • [2] BIKWAH A, 1989, J CHEM SOC CHEM COMM, P1160
  • [3] APPLICATION OF ULTRASOUND IN CARBOHYDRATE-CHEMISTRY - SYNTHESIS OF OPTICALLY PURE FUNCTIONALIZED HEXAHYDRO-ANTHRACENES AND HEXAHYDRO-NAPHTHACENES
    CHEW, S
    FERRIER, RJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) : 911 - 912
  • [4] CIGANEK E, 1984, ORG REACTIONS, P1
  • [5] 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
  • [6] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS
    COREY, EJ
    WINTER, RAE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) : 2677 - &
  • [7] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES
    DAVID, S
    HANESSIAN, S
    [J]. TETRAHEDRON, 1985, 41 (04) : 643 - 663
  • [8] DIFFERENTIAL USE OF THE PYRANOSIDE RING FOR STEREOCONTROLLED ROUTES TO TRIQUINANES - SILPHINENE AND SILPHIPERFOLENE SKELETA
    DICKSON, JK
    FRASERREID, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (20) : 1440 - 1443
  • [9] Fraser-Reid B., 1989, STRATEGIES TACTICS O, V2, P123
  • [10] SOME OBSERVATIONS ON THE RELATIVE REACTIVITIES OF ALPHA-ENONES OF OXANES AND CYCLOHEXANES
    FRASERREID, B
    UNDERWOOD, R
    OSTERHOUT, M
    GROSSMAN, JA
    LIOTTA, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) : 2152 - 2155