Synthetic Studies toward Highly Functionalized 5-Lanosterol Derivatives: A Versatile Approach Utilizing Anionic Cyclo

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• 作者：Sreekanth A. Ramachandran ; Rajendra K. Kharul ; Sylvain Marque ; Pierre Soucy ; Fré ; dé ; ric Jacques ; Robert Chê ; nevert ; Pierre Deslongchamps
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：August 4, 2006
• 年：2006
• 卷：71
• 期：16
• 页码：6149 - 6156
• 全文大小：181K
• 年卷期：v.71,no.16(August 4, 2006)
• ISSN：1520-6904

文摘

Stereoselective synthesis of the potentially biologically valuable 5-lanosteroidal-type backbone wasachieved via anionic cycloaddition. Synthesis of the two new bicyclic Nazarov intermediates 14 and 40and their cycloaddition with chiral cyclohexenone 25 and further functional group manipulations resultedin highly functionalized tetracyclic intermediates 28 and 44. These synthetic intermediates could lead tothe total synthesis of new lanosterol-based inhibitors.