An organocatalytic enantioselective synthesis of (+)-duryne

An efficient enantioselective synthesis of the potent anticancer agent (+)-duryne was achieved by the use of a one-pot organocatalyzed hydroxylation/Ohira–Bestmann and Grubbs cross-metathesis/selective cis-Wittig reaction. This new approach is envisioned to facilitate the synthesis of every representative member of the family.

An efficient enantioselective synthesis of potent anticancer agent (+)-duryne was achieved by means of one-pot organocatalyzed hydroxylation/Ohira–Bestmann and Grubbs cross-metathesis/selective cis-Wittig reactions.Figure optionsDownload as PowerPoint slide

(S)-1-(4-Methoxybenzyloxy)but-3-yn-2-olC12H14O3[α]D24=+3.0 (c 0.9, CHCl3)97% eeSource of chirality: organo-catalysisAbsolute configuration: (3S)

(S,E)-14-(4-Methoxybenzyloxy)-13-(methoxymethoxy) tetradec-11-enalC18H26O5[α]D24=+40.6 (c 0.75, CHCl3)Source of chirality: organo-catalysisAbsolute configuration: (13S)

(2S,3E,14Z,25E,27S)-2,27-Bis(methoxymethoxy)octacosa-3,14,25-triene-1,28-diolC32H60O6[α]D24=+34.6 (c 0.8, CHCl3)Source of chirality: organo-catalysisAbsolute configuration (2S,27S)