What question did this study set out to answer?

This research aims to synthesize and evaluate the neuroprotective properties of notopterol and its analogs.

July 6, 2026Organic Letters0 citations

Asymmetric Total Synthesis and Antihypoxic Neuroinflammatory Evaluation of Notopterol, Notoptol, and Their Natural Analogues

Key Points

This research aims to synthesize and evaluate the neuroprotective properties of notopterol and its analogs.
Conducted asymmetric total synthesis of notopterol, notoptol, and nine analogues using a gram-scale BTHL-catalyzed reaction.
Performed biological evaluations to identify neuroinflammatory activity in response to hypoxia.
(−)-1 and (−)-3 demonstrated significant antihypoxic neuroinflammatory activity, indicating therapeutic promise.
Achieved high enantioselectivity (>98% ee) in the synthesis process.

Abstract

The first asymmetric total synthesis of bioactive furocoumarins notopterol ( 1 ), notoptol ( 8 ), and nine natural analogues is reported. It features a gram-scale, BTHL-catalyzed asymmetric vinylogous-Mukaiyama-aldol reaction (VMAR) with excellent enantioselectivity (>98% ee). A subsequent 1,3-rearrangement converts notopterol ( 1 ) to notoptol ( 8 ), suggesting a plausible biosynthetic relationship. This work represents the first application of the BTHL catalytic system to non-Brassard diene substrates. Biological evaluation identified (−)- 1 and (−)- 3 as potent, configuration-dependent antihypoxic neuroinflammatory agents, highlighting the value of the synthesis.

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