Tetrahedron p. 7353 - 7360 (1989)
Update date:2022-07-30
Topics: Synthesis Enantiomer Catalyst Stereochemistry Chromatography Reactant Pyrethroid
Yadav, J. S.
Mysorekar, Sudha V.
Rao, A. V. Rama
A synthesis of (1R)-(+)-cis-chrysanthemic acid from (R,R)-tartaric acid is described.The diol 8 was converted to the mono MEM protected compound 8b.Dehydration of the tertiary alcohol using methanesulfonyl chloride-triethylamine-DMAP and treatment of the resulting product with lithium in liquid ammonia afforded 10.The diazoester of 10 was subjected to intramolecular cyclopropanation using a soluble copper complex to obtain 12.Cleavage of the MEM ether, dehydration of the tertiary alcohol followed by reductive cleavage with lithium in liquid ammonia gave the title compound.
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Doi:10.1016/j.tet.2011.01.066
(2011)Doi:10.1021/ic200143b
(2011)Doi:10.1248/cpb.40.2377
(1992)Doi:10.1016/j.bioorg.2018.07.009
(2018)Doi:10.1016/j.tetlet.2011.01.043
(2011)Doi:10.1016/0008-6215(89)85099-2
(1989)
