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Synlett
DOI: 10.1055/a-2738-7991
Letter

Asymmetric Total Synthesis of Streptoglycerides A and B

Authors

  • Virendra R Khobragade

    1   Organic Chemistry, CSIR - National Chemical Laboratory, Pune, India (Ringgold ID: RIN29616)

  • Archana AR

    1   Organic Chemistry, CSIR - National Chemical Laboratory, Pune, India (Ringgold ID: RIN29616)

  • Chepuri Venkata Ramana 

    2   ORGANIC CHEMISTRY, CSIR - National Chemical Laboratory, Pune, India (Ringgold ID: RIN29616)

Supported by: Science and Engineering Research Board CRG/2021/005729
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A unified strategy for the asymmetric total synthesis of streptoglycerides A and B has been established and confirmed their proposed absolute configurations. Key to our strategy is the synthesis of bicyclic scaffold employing a gold-catalyzed cascade cyclization of 1,6 diyn ol operating through a 6 endo/5 exo dig mechanism and its one-pot dihydroxylation followed trans-glycosylation to forge the central tricyclic core of these natural products. The Noyori’s asymmetric transfer hydrogenation of an α,β acetylenic ketones has been employed to install the key propargyl alcohol center with the desired absolute configuration. The pendant conjugated trans-1,3,5-triene/trans-1,3-diene side chains were introduced from a propanaldehyde unit following [Pd]-catalysed oxidative dehydrogenation and/or Takai olefination and Stille cross-coupling.



Publication History

Received: 23 September 2025

Accepted after revision: 04 November 2025

Accepted Manuscript online:
04 November 2025

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