Total Synthesis of (+)-Lysergic Acid

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• 作者：Qiang Liu ; Yu-An Zhang ; Ping Xu ; Yanxing Jia
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：November 1, 2013
• 年：2013
• 卷：78
• 期：21
• 页码：10885-10893
• 全文大小：474K
• 年卷期：v.78,no.21(November 1, 2013)
• ISSN：1520-6904

文摘

We report the enantioselective total synthesis of (+)-lysergic acid using two different strategies, which featured three metal-catalyzed reactions for the construction of the BCD three rings, involving Pd-catalyzed indole synthesis for the construction of the B ring, a ring-closing metathesis reaction for the formation of the D ring, and an intramolecular Heck reaction to forge the C ring. In synthetic strategy I, the synthesis was achieved in 20 steps following the ring construction sequence of BDC. In synthetic strategy II, the synthetic route was shortened to only 12 steps by following the ring construction sequence of DBC and using a 4-chlorotryptophan derivative for the intramolecular Heck reaction. Moreover, we also discussed an unsuccessful synthetic strategy.