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

doi:10.1002/HLCA.201500525

Paper

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

Published May 1, 2016 · Jorgelina L. Pergomet, T. Kaufman, Andrea B. J. Bracca

Helvetica Chimica Acta

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Abstract

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.

Study Snapshot

This study presents a straightforward approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for synthesizing TMC 120-B, pseudodeflectusin, and other natural products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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