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May 2, 2026ChemistrySelect0 citations

Total Synthesis of Coniferin B, Butylconiferin, and Coniferin Via a Reductive Acetal Ring‐Opening Reaction

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HYHuiwen YangXYXiangdi YaoRLRuipeng Li

Key Points

  • The aim is to synthesize Coniferin B and related compounds from vanillin for potential antiHIV activity.
  • Used a four-step linear synthesis starting from commercial vanillin.
  • Incorporated pivotal Schmidt O-glycosylation and Wittig reaction.
  • Conducted preliminary docking studies to analyze binding with carbonic anhydrase XII.
  • Coniferin B synthesis achieved a 10% overall yield.
  • Synthesis of trans Coniferin and Butylconiferin yielded 43% and 21%, respectively.
  • Docking studies suggest potential interaction with carbonic anhydrase XII.

Abstract

ABSTRACT Herein, we report the first total synthesis of the antiHIV natural product Coniferin B via a concise four‐step linear sequence from commercial vanillin. The strategy features a pivotal Schmidt O ‐glycosylation and a Wittig reaction, culminating in a reductive acetal ring‐opening. This efficient route affords Coniferin B in 10% overall yield and was successfully extended to the synthesis of the related compounds trans Coniferin and Butylconiferin in 43% and 21% yield, respectively. Preliminary docking studies were conducted to explore a potential binding mode, suggesting that the synthetic target Coniferin B may interact with carbonic anhydrase XII (5MSB).

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Cite This Study

Yang et al. (2026) studied this question.

synapsesocial.com/papers/69f5941871405d493affeebbhttps://doi.org/10.1002/slct.202506979
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