Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy

Autor:	Rajesh Viswanathan, Vasily A. Ignatenko, Ping Zhang
Rok vydání:	2011
Předmět:	Indole test Reaction mechanism Stereochemistry Organic Chemistry Substituent Biochemistry Combinatorial chemistry Redox Chemical synthesis chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Isoprene
Zdroj:	Tetrahedron Letters. 52:1269-1272
ISSN:	0040-4039
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c49f3fbdeabb2c4a917b232713d58d2c https://doi.org/10.1016/j.tetlet.2011.01.020 Zobrazit plný text záznamu Full Text from ScienceDirect