4423-79-4Relevant articles and documents
The first enantioselective synthesis of palinurin
Perez, Manuel,Perez, Daniel I.,Martinez, Ana,Castro, Ana,Gomez, Generosa,Fall, Yagamare
supporting information; experimental part, p. 3252 - 3254 (2009/12/01)
The first enantioselective synthesis of palinurin has been accomplished starting from commercially available furaldehyde and (R)-methyl-3-hydroxy-2- methylpropionate; the key steps of the synthesis include the use of a chiral pyrrolidine to create the chiral tetronic moiety, and Horner-Wadsworth-Emmons, Wittig and Wittig-Horner reactions to construct the alkene units.
Dioxalanones as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-Deoxy-D-Arabino-2-Heptulosonic acid (DAH) and 2-Keto-3-Deoxy-D-Gluconic acid (KDG)
Ramage, Robert,MacLeod, Angus M.,Rose, Graeme W.
, p. 5625 - 5636 (2007/12/18)
Three biosynthetically significant α-keto acids KDO (7), DAH (8) and KDG (9) have been synthesised via 5-ylidene-1,3-dioxalan-4-one intermediates formed by Wittig reactions of protected monosaccharide-derived aldehydes with the Wittig reagent (3).
Dioxolanones as Synthetic Intermediates. Part 4. Biomimetic Synthesis of Multicolanic Acid
Ramage, Robert,McCleery, Patrick P.
, p. 1555 - 1560 (2007/10/02)
Regiospecific cyclisation of the intermediate formed by reaction of the dioxolanone (9) with methyl α-lithioheptanoate gave (Z)-t-butyl multicolanate (13) in 53percent yield.Photochemical stereomutation of (13) gave (E)-t-butyl multicolanate (16) which was converted by trifluoroacetic acid into (E)-multicolanic acid (3), a metabolite of P. multicolor.In the same way, reaction of (9) with methyl α-lithiophenylacetate and, if desired, subsequent photochemical irradiation, provided (Z)- and (E)-4-carboxymethylene-2-phenyltetronic acids (21) and (23).