Synthetic investigation demonstrates the first asymmetric total synthesis of gymnothespirolignan A in 11 steps, highlighting a general route toward diverse spirocyclic gymnothelignans.
The first asymmetric total synthesis of gymnothespirolignan A is disclosed in 11 steps. The salient feature of the synthesis is construction of the spirocyclic moiety through a bioinspired acid-promoted double cyclization of an acyclic gymnothebutyllignan A-like precursor, which involves a deprotection, hemiketalization, dehydrative oxonium formation, and Friedel-Crafts cyclization cascade transformation. This study provides a general approach to the asymmetric syntheses of novel spirocyclic gymnothelignans.
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Yang et al. (2025) studied this question.
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