Total Synthesis of (−)-Sigillin A: A Polychlorinated and Polyoxygenated Natural Product

Autor:	Shota Kawai, Kiyosei Takasu, Takamori Nakayama, Yousuke Yamaoka
Rok vydání:	2020
Předmět:	chemistry.chemical_compound Natural product chemistry 010405 organic chemistry Organic Chemistry Total synthesis Organic chemistry Physical and Theoretical Chemistry Skeleton (category theory) 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences
Zdroj:	Organic Letters. 22:7721-7724
ISSN:	1523-7052 1523-7060
Popis:	The total synthesis of (−)-sigillin A, a highly chlorinated and oxygenated octahydroisocoumarin, is described herein. A hexahydroisocoumarin skeleton was constructed from (R)-4-(trichloromethyl)oxetan-2-one in seven steps. Its unique manganese oxidation provided an enone as the key intermediate of sigillin A. Stereoselective installation of two hydroxy groups and formation of gem-dichloroalkene from the corresponding ketone led to the total synthesis of (−)-sigillin A in a total of 16 steps.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3ff3eb951603cadadf25734384258b73 https://doi.org/10.1021/acs.orglett.0c02930 Zobrazit plný text záznamu