302348-74-9Relevant academic research and scientific papers
An enantioselective total synthesis of phomopsolide C
Harris, Joel M.,O'Doherty, George A.
, p. 8195 - 8199 (2007/10/03)
A flexible enantioselective route to highly functionalized α,β-unsaturated δ-lactones, has allowed for the synthesis of phomopsolide C. This approach derives its asymmetry from (S)-lactic acid and by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran. The resulting diols are produced in high enantioexcess and can be stereoselectively transformed into α,β-unsaturated-δ-lactones via a short highly diastereoselective oxidation and reduction sequence. A Wittig olefination reaction was used to introduce the side chain in either cis or trans form that was further elaborated into phomopsolide C.
An olefination approach to the enantioselective syntheses of several styryllactones
Harris, Joel M,O'Doherty, George A
, p. 5161 - 5171 (2007/10/03)
A flexible enantioselective route to highly functionalized α,β-unsaturated δ-lactones, has allowed for the syntheses of the styryllactones: altholactone, isoaltholactone, 3-epi-altholactone, 2-epi-altholactone and 5-hydroxy goniothalamin in 2.5, 10, 5, 1 and 13% overall yields from furfural, respectively. This approach derives its asymmetry by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran. The resulting diols are produced in high enantioexcess and can be stereoselectively transformed into α,β-unsaturated-δ-lactones via a short highly diastereoselective oxidation and reduction sequence. Wittig olefination or Julia olefination reactions were used to introduce the phenyl group side chain either cis or trans selectively and these intermediates were further elaborated into the altholactone isomers via selective epoxidation reactions.
Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin
Harris, Joel M.,O'Doherty, George A.
, p. 2983 - 2986 (2007/10/03)
A flexible enantioselective route to highly functionalized γ,β-unsaturated δ-lactones has allowed for the syntheses of the styryllactones: isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin in 10%, 5%, and 13% overall yields from furfural, re
