- 作者: 陳繼明;Dwight S. Fullerton
- 作者服務機構: 私立臺北醫學院藥物化學科; 美國?立崗州立大學藥學院藥物化學科
- 中文摘要: Trichothecene抗生素於化學構造與作用關係研究中,3-Hydroxy-10-methyl-cis-hexahydrochroman-7-one(2)為必 備之中間物,而有做?trichothecene全合成前驅物質的可能性;本研究主要就此物質之製備尋求一種簡易且具有立體選擇 性之方法。 Bicyclic enone 8轉變?ketal 9後,經Cr03-pyridine氧化得enone ketal 10 , LiAlH4還原,酯化形成acetate 10b, 通入臭氧氧化雙鍵及NaBH4還原後,於酸性催化下,合環形成目的化合物2 ;最後合環時形成「順環」?一種分子內 Michael型之反應,且具有立體選擇性存在。
- 英文摘要: A facile synthsis of 3-hydroxy-10-methyl-cis-hexahydrochroman-7-one (2), a promising synthetic precursor for the trichothecene antibiotics as explored. Direct dioxolanation of bicyclic enone 8 followed by allylic oxidation gave the enone ketal 9. The latter was reduced with LiAlH4 and acetylated to acetate 10b. Ozonolysis of the double bond followed by NaBH4 reduction gave diol 11 which subsequently cyclized to cis-fused target compound 2 by acid catalysis. The stereoselective formation of the cis-fused ring juncture is found to be an intramolecular Michael cyclization.
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