Regioselective and diastereoselective amination with use of chlorosulfonyl isocyanate: a short and efficient synthesis of (-)-cytoxazone |
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Authors: | Kim Ji Duck Kim In Su Jin Cheng Hua Zee Ok Pyo Jung Young Hoon |
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Affiliation: | College of Pharmacy, Sungkyunkwan University, Suwon 440-746, Korea. |
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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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