ol5b01888_si_001.pdf (1.87 MB)
Total Synthesis of Aquatolide
journal contribution
posted on 2015-08-07, 00:00 authored by Jordy
M. Saya, Klaas Vos, Roel A. Kleinnijenhuis, Jan H. van Maarseveen, Steen Ingemann, Henk HiemstraA total synthesis of the sesquiterpene
lactone aquatolide has been
accomplished. The central step is an intramolecular [2 + 2]-photocycloaddition
of an allene onto an α,β-unsaturated δ-lactone.
Other key steps are an intramolecular Horner–Wadsworth–Emmons
reaction to close the lactone and an intramolecular Mukaiyama-type
aldol reaction to cyclize the eight-membered ring. Racemic aquatolide
has been resolved using preparative HPLC.
