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
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 38期
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.
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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 [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
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 [J].
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 .
JOURNAL OF ANTIBIOTICS, 1992, 45 (05) :639-647
[5]   THE ZARAGOZIC ACIDS - STRUCTURE ELUCIDATION OF A NEW CLASS OF SQUALENE SYNTHASE INHIBITORS [J].
HENSENS, OD ;
DUFRESNE, C ;
LIESCH, JM ;
ZINK, DL ;
REAMER, RA ;
VANMIDDLESWORTH, F .
TETRAHEDRON LETTERS, 1993, 34 (03) :399-402
[6]   THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .2. STRUCTURE ELUCIDATION [J].
SIDEBOTTOM, PJ ;
HIGHCOCK, RM ;
LANE, SJ ;
PROCOPIOU, PA ;
WATSON, NS .
JOURNAL OF ANTIBIOTICS, 1992, 45 (05) :648-658
[7]  
WATSON NS, UNPUB J BIOORG MED C
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