224580-59-0Relevant academic research and scientific papers
Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B
Aggarwal, Varinder K.,Bae, Imhyuck,Lee, Hee-Yoon
, p. 9725 - 9733 (2007/10/03)
Catalytic and stoichiometric asymmetric sulfur ylide reactions were employed to prepare alkyl-aryl epoxide intermediates in a convergent manner. These epoxides were utilized in efficient syntheses of the mevinic acid analogue 1 and prelactone B. Graphical abstract.
Enantioselective Synthesis of γ,δ-Disubstituted β-Hydroxy δ-Lactones from Furans: Synthesis of (+)-Prelactone B and its C-4 Epimer
Csák?, Aurelio G.,Mba, Myriam,Plumet, Joaquín
, p. 2092 - 2094 (2007/10/03)
A new method for the enantioselective synthesis of γ,δ- disubstituted β-hydroxy δ-lactones (5,6-dialkyl-5,6-dihydropyran-2- ones) is reported and exemplified for (+)-prelactone B and its C-4 epimer. Our approach is based on the ring-enlargement of suitably functionalized optically pure 4-hydroxycyclopentanones, which are readily obtained from chiral 4-hydroxycyclopent-2-enones derived from furans. The procedure is amenable to the large-scale synthesis of the title compounds.
Synthesis of prelactone B
Hanefeld,Hooper,Staunton
, p. 401 - 403 (2007/10/03)
Prelactone B (1a) and its isomer 1b are possible products of a truncated avermectin polyketide synthase. In order to make them available as reference compounds they were synthesized in a six-step synthesis with 56% overall yield.
