Astracondensatol D (), a pentacyclic triterpenoid featuring an uncommon 6/6/5/6-fused ring system, along with its precursor astracondensatol E (), and two simplified 20(27)-octanorcycloastragenol derivatives ( and ) were isolated from for the first time. Classical NMR spectroscopic data, integrated with NMR and DP4+ calculations, unambiguously determined their absolute stereostructures. X-ray crystallography provided independent confirmation of the structure of compound . The plausible biosynthetic pathway, encompassing the Wagner-Meerwein rearrangement and retro-aldol reaction, was proposed for their formation and supported by computational analysis.
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http://dx.doi.org/10.1021/acs.orglett.5c00282 | DOI Listing |
Org Lett
March 2025
National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Mississippi 38677, United States.
Astracondensatol D (), a pentacyclic triterpenoid featuring an uncommon 6/6/5/6-fused ring system, along with its precursor astracondensatol E (), and two simplified 20(27)-octanorcycloastragenol derivatives ( and ) were isolated from for the first time. Classical NMR spectroscopic data, integrated with NMR and DP4+ calculations, unambiguously determined their absolute stereostructures. X-ray crystallography provided independent confirmation of the structure of compound .
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