The Journal of Organic Chemistry

Synthetic anthracyclinones. 15. An improved route to 8-demethoxyaranciamycinone and synthesis of the. alpha.-L-daunosamine glycosides

K Krohn, E Broser

文献索引：Krohn, Karsten; Broser, Erwin Journal of Organic Chemistry, 1984 , vol. 49, # 20 p. 3766 - 3771

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被引用次数: 15

摘要

For the new reaction sequence an efficient synthesis for 7-methyljuglone (7) had to be developed. Derivative 7 is a naturally occurring naphthoquinone (ramenta~ etone)~ and earlier syntheses gave only unsatisfactory yields. lOJ1 Reaction of benzoquinone (3) with 3- methyl-l-(tri-methylsiloxy)-l, 3-butadiene (4Yb led to 5 which was converted to 7 by acid treatment and PCC oxidation in 58% overall yield (Scheme I). Since 5 and 6 are rather ...