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  • Title: Regioselective and diastereoselective amination with use of chlorosulfonyl isocyanate: a short and efficient synthesis of (-)-cytoxazone.
    Author: Kim JD, Kim IS, Jin CH, Zee OP, Jung YH.
    Journal: Org Lett; 2005 Sep 01; 7(18):4025-8. PubMed ID: 16119958.
    Abstract:
    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]
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