Regioselective and diastereoselective amination with use of chlorosulfonyl isocyanate: a short and efficient synthesis of (-)-cytoxazone.

Autor: Kim JD; College of Pharmacy, Sungkyunkwan University, Suwon 440-746, Korea., Kim IS, Jin CH, Zee OP, Jung YH
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2005 Sep 01; Vol. 7 (18), pp. 4025-8.
DOI: 10.1021/ol0515255
Abstrakt: The total synthesis of (-)-cytoxazone 1 was achieved in six linear steps (34% overall yield) from p-anisaldehyde. The key steps in this route are the regioselective and stereoselective introduction of a N-protected amine group, using the CSI reaction of the anti-1,2-dimethyl ether 3, and the subsequent regioselective cyclization of the N-protected amino diol 13 to give the 2-oxazolidinone unit of (-)-cytoxazone 1. [reaction: see text]
Databáze: MEDLINE