Regioselective and diastereoselective amination with use of chlorosulfonyl isocyanate: a short and efficient synthesis of (-)-cytoxazone.
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]
Kim
Ji Duck
JD
College of Pharmacy, Sungkyunkwan University, Suwon 440-746, Korea.
Kim
In Su
IS
Jin
Cheng Hua
CH
Zee
Ok Pyo
OP
Jung
Young Hoon
YH
D000586:Amination; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D017953:Isocyanates; D010080:Oxazoles; C117832:cytoxazone