A SHORT SYNTHESIS OF DEOXYFRENOLICIN

被引:43
作者
BRIMBLE, MA [1 ]
LYNDS, SM [1 ]
机构
[1] MASSEY UNIV,DEPT CHEM & BIOCHEM,PALMERSTON NORTH,NEW ZEALAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 05期
关键词
D O I
10.1039/p19940000493
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative rearrangement of furo[3,2-b]naphtho[2,1-d]furan 8 using CAN provided an efficient route to the hemiacetal 9 which has a three-ring system in common with that in the natural products frenolicin A 1, frenolicin B 2 and deoxyfrenolicin 3. Attempted reduction of the hemiacetal 9 to the cis-lactone 11 using triethylsilane and trifluoroacetic acid was unsuccessful, however, hydrogenation of the hemiacetal 9 not only effected reduction of the hemiacetal group to a cyclic ether but also hydrogenolysis of the gamma-lactone to the ring-opened carboxylic acid which was conveniently characterised as its methyl ester 13. Deprotection of the methyl ether 13 to the naphthol 15 using boron tribromide also effected cis-trans epimerisation at C-1 thus completing a synthesis of deoxyfrenolicin 3 upon hydrolysis of the methyl ester to the carboxylic acid.
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页码:493 / 496
页数:4
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