Superacid cyclization of (2 E ,6 E ,10 E ,14 E )-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether

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• 作者：V. Kulcitki ; M. Grin’ko ; A. Barba ; N. Ungur and P. F. Vlad
• 关键词：superacid cyclization ; sesquiterpenoids ; terpenylphenylsulfones ; synthesis
• 刊名：Chemistry of Natural Compounds
• 出版年：2007
• 出版时间：May, 2007
• 年：2007
• 卷：43
• 期：3
• 页码：268-273
• 全文大小：46 KB
• 刊物类别：Medicine
• 刊物主题：Pharmacy
  Organic Chemistry
  Plant Sciences
  Russian Library of Science
  
• 出版者：Springer New York
• ISSN：1573-8388

文摘

A mixture of (13E,17E)-12-phenylsulfonylbicyclogeranylfarnesol tetrahydropyranyl ether (8) and (13E,17E)-12-phenylsulfonylbicyclogeranylfarnesol (9) was formed by superacid low-temperature cyclization of exclusively trans-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether (1). The structures of 8 and 9 were established using spectral data. The optically active form of 9 was also confirmed by retrosynthesis from (+)-sclareolide (10).