Expedient Approach to 6-Bromo-2-isopropylidenecoumaranone, a Potential Intermediate for the Synthesis of TMC-120B, Pseudodeflectusin, and Their Congeners

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 res...

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Bibliographic Details
Published in:Helvetica chimica acta 2016-05, Vol.99 (5), p.398-404
Main Authors: Pergomet, Jorgelina L., Kaufman, Teodoro S., Bracca, Andrea B. J.
Format: Article
Language:English
Subjects:
6-Bromo-2-isopropylidenecoumaranone
Natural product synthesis
Proline-mediated cyclization
Pseudodeflectusin
TMC-120B
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Summary: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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201500525