Asymmetric total synthesis of (+)-O-methylasparvenone, a rare nitrogen-free serotonin 2C receptor antagonist.

نویسندگان

  • Raphaël Lafleur-Lambert
  • John Boukouvalas
چکیده

The first enantioselective synthesis of the fungal metabolite (+)-O-methylasparvenone was achieved in eight steps and 22% overall yield from inexpensive 3,4,5-trimethoxybenzaldehyde dimethyl acetal. Key steps include (i) early-stage asymmetric alkynylation of an aromatic aldehyde with a propiolate, (ii) intramolecular Friedel-Crafts acylation, and (iii) site-selective cleavage of an aryl methyl ether.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 14 37  شماره 

صفحات  -

تاریخ انتشار 2016