Synthesis p. 659 - 661 (1987)
Update date:2022-07-30
Topics: Synthesis Ketone Experimental phosphorus β-ketophosphonate
Mikolajczyk, Marian
Balczewski, Piotr
Methylenomycin B (1) was prepared from diethyl 2-oxopropanephosphonate (5) in four steps in 26percent yield.The key steps in this synthesis include the Wittig-Horner reaction of 5 with methylthioethanal (7) followed by the 1,4-addition of a propionyl anion equivalent to the α-enone 4 formed affording 4-(methylthiomethyl)-hepta-2,5-dione (3) which is an acyclic precursor of the title antibiotic.
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Doi:10.1021/ja01499a045
(1960)Doi:10.1016/j.jfluchem.2008.01.007
(2008)Doi:10.1007/BF00529371
(1992)Doi:10.1021/ja01145a079
(1951)Doi:10.1021/om00097a003
(1988)Doi:10.1002/jhet.5570250406
(1988)
