Plausible reaction path for haval-argade contrathermodynamic rearrangement in synthesis of farinomalein
This work reports, the plausible reaction path in context of the farinomalein (1) and isofarinomalein (2) synthesized via Stobbe condensation and Haval-Argade Contrathermodynamic Rearrangement.
Firke, Narayan P.,Markandeya, Anil G.,Konde Deshmukh, Rajendra S.,Pingale, Shirish S.
Synthesis of natural maleimides farinomaleins C-E and evaluation of their antifungal activity
A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides.
Synthesis of natural maleimides farinomaleins C-E and evaluation of their antifungal activity
A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides.
Improved synthesis of farinomalein and its analogs
A practical and convenient synthesis of the fungicidal natural compound farinomalein is described starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate, employing a Horner-Wadsworth-Emmons condensation as the key step. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.