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Synthesis 2007(24): 3886-3890
DOI: 10.1055/s-2007-990928
DOI: 10.1055/s-2007-990928
PAPER
© Georg Thieme Verlag Stuttgart · New YorkEnantioselective Total Synthesis of the Antifungal Agent (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one [1]
Further Information
Received
29 May 2007
Publication Date:
28 November 2007 (online)
Publication History
Publication Date:
28 November 2007 (online)

Abstract
An enantioselective route for the synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one is reported. The synthesis is based on epoxide ring opening with a Grignard reagent and stereoselective reduction employing catecholborane as key reactions.
Key words
6-substituted 5,6-dihydro-2H-pyran-2-ones - catecholborane - antifungal activity
IICT Communication No. 061205
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Raoelison GE.Terreaux C.Queiroz EF.Zsila F.Simonyi M.Antus S.Randriantsoa A.Hostettmann K. Helv. Chim. Acta 2001, 84: 3470 - 3a
Fujita T.Nishimura H.Kaburagi K.Mizutani J. Phytochemistry 1994, 36: 23 - 3b
Nyandat E.Rwekika E.Galeffi C.Palazzino G.Nicoletti M. Phytochemistry 1993, 33: 1493 - 3c
Andrianaivoravelona JO.Sahpaz S.Terreaux C.Hostettmann K.Stoeckli-Evans H.Rasolondramanitra J. Phytochemistry 1999, 52: 265 - 3d
Pereda-Miranda R.Garcia M.Delgado G. Phytochemistry 1990, 29: 2971 - 4
Chandrasekhar S.Narsihmulu Ch.Sultana SS.Reddy MS. Tetrahedron Lett. 2004, 45: 9299 - 5a
Sabitha G.Sudhakar K.Reddy N. M.Rajkumar M.Yadav JS. Tetrahedron Lett. 2005, 46: 6567 - 5b
Sabitha G.Narjis F.Swapna R.Yadav JS. Synthesis 2006, 2879 - 5c
Sabitha G.Reddy EV.Yadagiri K.Yadav JS. Synthesis 2006, 3270 - 5d
Sabitha G.Bhikshapathi M.Yadav JS. Synth. Commun. 2007, 37: 561 - 5e
Sabitha G.Bhaskar V.Yadav JS. Tetrahedron Lett. 2006, 47: 8179 - 5f
Sabitha G.Sudhakar K.Yadav JS. Tetrahedron Lett. 2006, 47: 8599 - 5g
Sabitha G.Swapna R.Reddy EV.Yadav JS. Synthesis 2006, 4242 - 5h
Sabitha G.Gopal P.Yadav JS. Synth. Commun. 2007, 37: 1495 - 6
Simpson TJ.Smith RW.Westaway SM.Willis CL. Tetrahedron Lett. 1997, 38: 5367 - 7
Evans DA.Hoveyda AH. J. Org. Chem. 1990, 55: 5190
References
IICT Communication No. 061205