Absolute configuration and total synthesis of (−)-cabenegrin A-I

Autor:	György Litkei, Csaba Szántay, Adrienne L. Tőkés, LászlóL. Darkó, Katalin Gulácsi, Eszter Baitz-Gács, Sándor Antus
Rok vydání:	1999
Předmět:	Chiral auxiliary Stereochemistry Organic Chemistry Absolute configuration Total synthesis Resorcinol Biochemistry Medicinal chemistry Isocyanate chemistry.chemical_compound Természettudományok chemistry Drug Discovery Phenol Homochirality Kémiai tudományok Sesamol
Zdroj:	Tetrahedron. 55:9283-9296
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00490-1
Popis:	The total synthesis of (−)-cabenegrin A-I [(−)- 1 ] in five steps was achieved from (−)-6a R ,11a R -maackiain [(−)- 5 ], which in turn was prepared by the optical resolution of racemic (±)- 5 using S -(−)- α -methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of (−)-maackiain [(−)- 5 ] and (−)-cabenegrin A-I [(−)- 1 ] was proved by CD measurements. Synthesis of (±)-maackiain [(±)- 5 ] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b87f886b74084d4cde4d86c3672f3962 https://doi.org/10.1016/s0040-4020(99)00490-1 Zobrazit plný text záznamu Full Text from ScienceDirect