Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
2016
A straightforward approach toward 6-bromo-2-isopropylidenecoumaranone, a potential intermediate toward alkaloid TMC
120-B, pseudodeflectusin, and other natural products, was reported. The synthetic sequence involved the reaction of
3-bromosalicylaldehyde with chloroacetone and cyclization of the resulting ether to a 2-acetylcoumaranol intermediate. This
was followed by sequential methyl Grignard addition and Jones’ oxidation to the corresponding coumaranone, which was
dehydrated to the final product with the methanesulfonyl chloride/pyridine reagent. The protection of the coumaranol as the
corresponding THP-ether resulted in improved product yields.
Keywords:
- Correction
- Source
- Cite
- Save
- Machine Reading By IdeaReader
30
References
4
Citations
NaN
KQI