A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

Autor:	Kazuhiko Orito, Kouhei Goto, Masao Hino, Takashi Tokuhashi, Tomiki Takahashi, Harumi Kaga
Rok vydání:	1996
Předmět:	Allylic rearrangement Organic Chemistry Malonic acid Cyanation Biochemistry Claisen rearrangement chemistry.chemical_compound Capillary electrophoresis chemistry Drug Discovery Organic chemistry Stereoselectivity Orthoester Vanillylamine
Zdroj:	Tetrahedron. 52:8451-8470
ISSN:	0040-4020
DOI:	10.1016/0040-4020(96)00414-0
Popis:	Capsaicin, a main pungent principle of hot pepper, and its 15 analogs have been efficiently synthesized. The key step of this synthetic sheme is the orthoester Claisen rearrangement, which transformed allylic alcohols 2A-C to (E)-alkenoates 3A-C ( E Z > 100 ) in a highly stereoselective manner. The subsequent carbon chain elongations on 3 based on the cyanation or the malonic acid ester synthesis afforded (E)-alkenoic acids 8, which were converted to the corresponding acid chloride and then coupled with vanillylamine to give capsaicinoids. HPLC and CE (capillary electrophoresis) analyses of these capsaicinoids were also carried out.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::028d595404c12c8cbcd39659ab0ebb35 https://doi.org/10.1016/0040-4020(96)00414-0 Zobrazit plný text záznamu Full Text from ScienceDirect