Double furofuran annulation to a bis-naphthoquinone: an approach to dimeric pyranonaphthoquinones

被引:24
作者
Brimble, MA [1 ]
Duncalf, LJ [1 ]
Neville, D [1 ]
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 24期
关键词
D O I
10.1039/a805031g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of bis-naphthoquinone 7, a key intermediate in the synthesis of dimeric pyranonaphthoquinones related to the actinorhodins is described. Initial efforts directed to 7 which focussed on a double Fries rearrangement of bis-acetate 14 to 2-acetylnaphthol 13 were low yielding. Use of a Stille coupling reaction between dimeric bromonaphthalene 20 and (alpha-ethoxyvinyl)tri-n-butyltin 19 as a means to introduce the acetyl groups at C-2 was also low yielding. The optimum route to bis-naphthoquinone 7 involved the synthesis of 2-acetylnaphthol 13 from bromide 25 using a Suzuki-Miyaura coupling. Addition of 2-trimethylsilyloxyfuran to bis-naphthoquinone 7 afforded the bis-annulation adducts 30,31 which underwent double oxidative rearrangement to bis-lactols 32,33. Reduction of the bis-lactols to bis-ethers 34,35 completed the first synthesis of a dimeric pyranonaphthoquinone.
引用
收藏
页码:4165 / 4173
页数:9
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