THE SQUALESTATINS - C-3 DECARBOXYLATION STUDIES AND REARRANGEMENT TO THE 6,8-DIOXABICYCLO[3.2.1]OCTANE RING-SYSTEM

被引:16
作者
CHAN, C
INGLIS, GGA
PROCOPIOU, PA
ROSS, BC
SRIKANTHA, ARP
WATSON, NS
机构
[1] Department of Medicinal Chemistry, Glaxo Group Research Ltd., Greenford, Middlesex UB6 0HF, Greenford Road
关键词
D O I
10.1016/S0040-4039(00)61752-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Decarboxy squalestatins 3 and 4 were synthesised via photolysis of t-butyl peroxyester 7. Lactol 10 was isolated unexpectedly from both HCl-dioxan cleavage of 8, a by-product of the photolysis, and attempted Barton decarboxylation of 6. In TFA under anhydrous conditions, 8 was converted to the tricyclic ether 11.
引用
收藏
页码:6143 / 6146
页数:4
相关论文
共 7 条
  • [1] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS
    BARTON, DHR
    CRICH, D
    MOTHERWELL, WB
    [J]. TETRAHEDRON, 1985, 41 (19) : 3901 - 3924
  • [2] BAXTER A, 1992, J BIOL CHEM, V267, P11705
  • [3] Crich D., 1987, ALDRICHIM ACTA, V20, P35
  • [4] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY
    DAWSON, MJ
    FARTHING, JE
    MARSHALL, PS
    MIDDLETON, RF
    ONEILL, MJ
    SHUTTLEWORTH, A
    STYLLI, C
    TAIT, RM
    TAYLOR, PM
    WILDMAN, HG
    BUSS, AD
    LANGLEY, D
    HAYES, MV
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (05) : 639 - 647
  • [5] THE ZARAGOZIC ACIDS - STRUCTURE ELUCIDATION OF A NEW CLASS OF SQUALENE SYNTHASE INHIBITORS
    HENSENS, OD
    DUFRESNE, C
    LIESCH, JM
    ZINK, DL
    REAMER, RA
    VANMIDDLESWORTH, F
    [J]. TETRAHEDRON LETTERS, 1993, 34 (03) : 399 - 402
  • [6] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .2. STRUCTURE ELUCIDATION
    SIDEBOTTOM, PJ
    HIGHCOCK, RM
    LANE, SJ
    PROCOPIOU, PA
    WATSON, NS
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (05) : 648 - 658
  • [7] WATSON NS, UNPUB J BIOORG MED C