Biomimetic Synthesis of (+)-Neroplofurol.

(+)-Neroplofurol was biomimetically synthesized in only two steps from natural (+)-nerolidol via Sharpless dihydroxylation and a cascade Shi epoxidation/epoxide ring-opening reaction. All carbons are derived from natural (+)-nerolidol and no protecting groups were utilized, making the synthesis atom-economical and highly efficient. The synthetic neroplofurol was proved to be the enantiomer of the natural one, according to ¹H NMR, ¹³C NMR spectra and optical rotation value. The absolute configuration of natural neroplofurol was also deduced to be 3R,6S,7R,10S. [ABSTRACT FROM AUTHOR]