1280171-15-4Relevant articles and documents
Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy
Ignatenko, Vasily A.,Zhang, Ping,Viswanathan, Rajesh
supporting information; experimental part, p. 1269 - 1272 (2011/04/17)
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.