Synthesis of Rings DEF of Solanoeclepin A

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• 作者：Hsiang-Yu Chuang ; Minoru Isobe
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 17, 2017
• 年：2017
• 卷：82
• 期：4
• 页码：2045-2058
• 全文大小：700K
• ISSN：1520-6904

文摘

An improved synthesis of rings DEF of solanoeclepin A has been achieved from ent-Hajos Parrish ketone. A key tricyclo[5.3.2.0^1,6]decene intermediate having an additional vinyl group as a precursor of a hydroxyl functionality was synthesized, in which the key steps included (i) a [2,3]-Wittig rearrangement to provide trans-hydroindene with C11(R)-configuration, (ii) the introduction of a vinyl group as a masked OH at C6, (iii) an oxymercurative aldol to synthesize the tricyclo[5.3.2.0^1,6]decene moiety, (iv) an oxidative C–C bond cleavage to yield an aldehyde and an unsaturated methyl ketone, and (v) a radical cyclization for the cyclobutane ring formation to provide the tricyclo[5.2.1.0^1,6]decene compound.