Abstract
An efficient and practical route for the synthesis of (-)-tasimelteon from 2,3-bis(2-hydroxyethyl)phenol has been developed. The product was prepared in seven steps in overall 16.4% yield using highly stereoselective cyclopropanation reaction of the intermediate as the key step.
References
1.
Steven W.
,
Marlene A.
, and
Louis L.
, The Lancet , 2015 , 386 , 1754 .
2.
Rao M.
,
Yang M.
, and
Kuehner D.
, Org. Process. Res. Dev. , 2003 , 7 , 547 .
3.
Chen B.C.
,
Sundeen J. E.
,
North J. T.
,
Pullockaran A. J.
,
Ahmad S.
,
Wu S. C.
,
Atwal K. S.
, and
Durgar S.
, U.S. Patent: 6160134, issued date 12 December 2000.
4.
Prasad J.S.
,
Vu T.
,
Totleben M. J.
,
Crispino G. A.
, and
Kacsur D. J.
, Org. Process. Res. Dev. , 2003 , 7 , 821 .
5.
Singh A.K.
,
Rao M. N.
,
Simpson J. H.
,
Li W. S.
, and
Thornton J. E.
, Org. Process. Res. Dev. , 2002 , 6 , 618 .
6.
Deepak P.
, and
Platt N. M.
, W.O. Patent: 123389, issued date 20 August 2015 .
7.
Catt J.D.
,
Johnson G.
,
Keavy D. J.
,
Mattson R. J.
,
Parker M. F.
,
Takaki K. S.
, and
Yevich J. P.
, U.S. Patent: 5856529, issued date 5 November 1999 .
8.
Limnios D.
, and
Kokotos C. G.
, J. Org. Chem. , 2014 , 79 , 4273 .
9.
Yao H.R.
, and
Richardson D. E.
, J. Am. Chem. Soc. , 2000 , 122 , 3220 .
10.
Wadsworth W.S. Jr
, and
Emmons W. D.
, J. Am. Chem. Soc. , 1961 , 83 , 1733 .
11.
Denney D.B.
,
Vill J. J.
, and
Boskin M. J.
, J. Am. Chem. Soc. , 1962 , 84 , 3944 .
12.
Liu Y.Z.
,
Zhang H. C.
, and
Liu J.
, C.N. Patent: 102675268, issued date 19 September 2012 .
