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Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57
Graphical Abstract
Figure 1: Structures of naturally occurring karrikins.
Scheme 1: i) P4S10, THF; ii) 2-chloropropionyl chloride, Et3N; iii) Ph3P, NaOAc, Ac2O.
Figure 2: Target compounds with highlighted positions of oxygen to sulfur exchange.
Scheme 2: i) Lawesson’s reagent, HMDO, toluene, MW irradiation, 120 °C, 60 min.
Scheme 3: i) P4S10 or Lawesson’s reagent, see table for conditions; ii) 2-chloropropionyl chloride, Et3N, DCM...
Scheme 4: i) LiHMDS, MeI, THF, −78 °C.
Scheme 5: i) a) NaOH, MeOH/H2O, rt, Amberlyst 15 [H+], b) AcOH 70% aq, reflux, 2 h; ii) a) EtOCOCl, pyridine,...
Scheme 6: i) Lawesson’s reagent, HMDO, toluene, MW irradiation (120 °C), 60 min.