Total synthesis of enantiopure 1,3-dimethylpyranonaphthoquinones including ventiloquinones E, G, L and eleutherin.
A new synthetic approach to enantiopure pyranonaphthoquinones is described. (S)-Mellein 10, prepared in 6 steps from (S)-propylene oxide 16, is converted stereospecifically to the (1R,3S)-dimethylpyran 15. The pyran 15 is then converted to the benzoquinone 14, which undergoes regiospecific Diels-Alder reactions with a variety of oxygenated butadienes to give pyranonaphthoquinones including ventiloquinones E, G, L, eleutherin and ent-deoxyquinone A.
Tewierik
Leonie M
LM
School of Chemistry, University of Melbourne, Victoria, Australia3010.
Dimitriadis
Christian
C
Donner
Christopher D
CD
Gill
Melvyn
M
Willems
Brendan
B
D001578:Benzopyrans / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry
D001578:Benzopyrans; D007202:Indicators and Reagents; D009285:Naphthoquinones; D011714:Pyrans; D011809:Quinones; C415044:eleutherin