Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B.
J Org Chem
; 82(7): 3463-3481, 2017 04 07.
Article
en En
| MEDLINE
| ID: mdl-28252297
ABSTRACT
The C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels-Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Pironas
Idioma:
En
Revista:
J Org Chem
Año:
2017
Tipo del documento:
Article
País de afiliación:
China