- 作者: 沙晉康 ; 何文岳
- 作者服務機構: 清華大學化學系
- 中文摘要: A general approach toward spiro[4.4]nonane structure based on the.alpha.-carbonyl radical cyclization has been developed. Efficient total synthesis of dimethyl gloiosiphone A (2) was achieved. Thus, alkylation of the anion of dimethylhydrazone of cyclopentanone with 5-iodopent-l-yne followed by hydrolysis gave ketone 4. Iodination of 4 via its TMS-enol ether yielded iodo ketone 7. Radical spiro-cyclization of 7 gave spiro ketone 10. Iodination of 10 afford iodo spiro ketone 23. Oxidation and iodination of 23 gave compound 24. Methylation of 24 furnished methoxy iodo enone 25. Substitution of iodide in 25 with methoxide produced dimethoxy enone 26. Allylic oxidation of 26 gave diketone 27. Treatment of 27 with OsO/sub 4/ and N- methylmorpholine N-oxide gave dihydroxy ketone 28. Methylation of the primary alcohol group in 28 afforded dimethyl gloiosiphone A (2).
- 英文摘要: --
- 中文關鍵字: Dimethyl Gloiosiphone A; Carbonyl Radical Cyclization; Spiro[4.4]Nonene
- 英文關鍵字: 二甲基gloiosiphoneA;羰基自由基環化作用;螺環[4.4]壬烯