Stereoselective construction of the pyrrolizidine bridgehead stereochemistry by the adjacent hydroxyl group in the synthesis of (+)-heliotridine and (−)-retronecine

Autor:	Yeun-Min Tsai, Kun-Liang Wu, Sea-Chuan Hong, Jie-Ming Huang
Rok vydání:	2004
Předmět:	Stereochemistry Organic Chemistry Total synthesis General Medicine Biochemistry Radical cyclization Stereocenter chemistry.chemical_compound chemistry Group (periodic table) Drug Discovery Pyrrolizidine Retronecine Stereoselectivity Heliotridine
Zdroj:	Tetrahedron Letters. 45:3047-3050
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2004.02.097
Popis:	Formal total synthesis of (+)-heliotridine ( 4 ) and total synthesis of (−)-retronecine ( 5 ) were accomplished by using ( S )-3-acetoxysuccinimide ( 6 ) as the common starting material. The stereogenic center of 6 ended up as C-1 in both alkaloids. The chiral centers at C-7a of the alkaloids were stereoselectively constructed through the help of the adjacent functionality at C-1. The B-rings of the alkaloids were formed through α-sulfonyl radical cyclizations.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::234909dff1f544205be4cf64f53c2149 https://doi.org/10.1016/j.tetlet.2004.02.097 Zobrazit plný text záznamu Full Text from ScienceDirect