Asymmetric synthesis of all the stereoisomers of tarchonanthuslactone
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Acknowledgements
We thank CSIR for a research Grant to V.K.S. and research fellowships to S.B. and S.S.
References and notes (15)
- et al.
Planta Med.
(2000) - et al.
J. Chem. Soc., Perkin Trans. 1
(1990)et al.Chem. Pharm. Bull.
(1990)et al.Tetrahedron: Asymmetry
(1996)et al.J. Org. Chem.
(2001)et al.J. Org. Chem.
(2002)et al.Eur. J. Org. Chem.
(2003) - et al.
Tetrahedron
(1996)et al.Tetrahedron Lett.
(2000)et al.J. Org. Chem.
(2003)et al.Arkivoc
(2003)et al.J. Org. Chem.
(2004) - et al.
Chem. Rev.
(2004)(2003) Synthesis
(1981)et al.Bull. Chem. Soc. Jpn.
(1976)- et al.
Fortschr. Chem. Org. Naturst.
(1989)Fortschr. Chem. Org. Naturst.
(1978)et al.J. Sci. Ind. Res. (India)
(1979)Phytochemistry
(1976) - et al.
Phytochemistry
(1979)
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