Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

Autor:	Filippo De Simone, Jerome Waser
Rok vydání:	2011
Předmět:	Indole test Reaction mechanism cyclization Chemistry Organic Chemistry Iminium Regioselectivity Total synthesis indoles alkaloids Chemical synthesis iminium Organic chemistry aminocyclopropanes Selectivity Aspidospermidine
Zdroj:	Synlett. 2011:589-593
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0030-1259553
Popis:	The regioselective and diastereoselective cyclization of acyliminium intermediates generated from aminocyclopropanes on unprotected indoles is presented. The recent results obtained in our group are compared with previous intermolecular reactions with aminocyclopropanes as well as with other cyclization methods involving iminium ions and unprotected indoles. A first speculative analysis of possible reaction mechanisms allows rationalizing the observed selectivity. The high potential of the method for the synthesis of natural alkaloids is demonstrated in the formal synthesis of aspidospermidine and the total synthesis of goniomitine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8dca50296ce33fc44f8573b7e90fb1ce https://doi.org/10.1055/s-0030-1259553 Zobrazit plný text záznamu