Unified approach to prenylated indole alkaloids: total syntheses of (−)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I

Autor:	Eduardo V. Mercado-Marin, Richmond Sarpong
Rok vydání:	2015
Předmět:	Indole test Natural product Bicyclic molecule Stereochemistry Notoamide I Stephacidin General Chemistry Isocyanate Chemistry chemistry.chemical_compound chemistry Prenylation Moiety Organic chemistry
Zdroj:	Chemical Science
ISSN:	2041-6539 2041-6520
DOI:	10.1039/c5sc01977j
Popis:	The first strategy that provides reverse-prenylated indole alkaloids that bear a characteristic bicyclo[2.2.2]diazaoctane as well as those that lack this structural motif is reported. A unified strategy for the synthesis of congeners of the prenylated indole alkaloids is presented. This strategy has yielded the first synthesis of the natural product (–)-17-hydroxy-citrinalin B as well as syntheses of (+)-stephacidin A and (+)-notoamide I. An enolate addition to an in situ generated isocyanate was utilized in forging a key bicyclo[2.2.2]diazaoctane moiety, and in this way connected the two structural classes of the prenylated indole alkaloids through synthesis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8cd69a1e0e677ee5deab9b35e61e6756 https://doi.org/10.1039/c5sc01977j Zobrazit plný text záznamu