Modular enantioselective synthesis of 8-aza-prostaglandin E1.
J Org Chem
; 78(18): 9488-93, 2013 Sep 20.
Article
en En
| MEDLINE
| ID: mdl-23957245
ABSTRACT
We report herein for the first time the enantioselective synthesis of 8-aza-PGE1. The synthesis used the cross olefin metathesis reaction to connect the 5-vinyl-γ-lactam subunit, prepared from (R)-malic acid via the Ley's sulfone-based α-amidalkylation protocol (dr = 6.81), with the chiral pre-ω-chain. The latter was synthesized in high enantioselectivity from (E)-2-octenol by the Sharpless asymmetric epoxidation and the titanocene-mediated epoxide opening. This modular approach is quite concise and flexible, and requires only eight steps from commercially available reagents.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Alprostadil
Idioma:
En
Revista:
J Org Chem
Año:
2013
Tipo del documento:
Article