Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy |
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Authors: | Vasily A IgnatenkoPing Zhang Rajesh Viswanathan |
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Institution: | Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA |
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Abstract: | A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C5 dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. |
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Keywords: | (± )-Debromoflustramine A Flustra foliacea Alkaloid NCS-mediated activation C3 reverse prenylation |
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