Stereocontrolled generation of the (2R) chroman core of vitamin E: total synthesis of (2R,4'RS,8'RS)-alpha-tocopherol.
Org Lett
; 11(21): 4930-3, 2009 Nov 05.
Article
em En
| MEDLINE
| ID: mdl-19863149
ABSTRACT
(2R,4'RS,8'RS)-alpha-tocopherol (1) was prepared using, as the two key steps, a novel diastereoselective TiCl(4)-promoted (S)-sulfoxide-directed allylation of ketal 2 with allyl trimethyl silane 3 to efficiently generate the challenging (2R) stereocenter of the chroman moiety and a cross-metathesis reaction with olefin 4 to efficiently join the lipophilic alkyl chain present in the final target.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Cromanos
/
Alfa-Tocoferol
Idioma:
En
Ano de publicação:
2009
Tipo de documento:
Article