Rapid Synthesis of the Spiroketal Subunit of Neaumycin B: Stereochemical Aspects of Singly Anomeric Spiroketals and Proposal for a Stereocenter Reassignment

Neaumycin B is a complex polyketide that shows phenomenal cytotoxicity against U87 glioblastoma cells. The singly anomeric spiroketal core is a notable subunit in the natural product’s structure. We report a rapid and convergent approach to the spiroketal group, resulting in the formation of two iso...

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Bibliographic Details
Published in:Organic letters 2024-12, Vol.26 (50), p.10774-10779
Main Authors: Healy, Anna E., Van Engen, Marcus D., Cinti, Nicholas A., Floreancig, Paul E.
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - pharmacology
Furans - chemical synthesis
Furans - chemistry
Furans - pharmacology
Humans
Letter
Molecular Structure
Polyketides - chemical synthesis
Polyketides - chemistry
Polyketides - pharmacology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Spiro Compounds - pharmacology
Stereoisomerism
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Summary:Neaumycin B is a complex polyketide that shows phenomenal cytotoxicity against U87 glioblastoma cells. The singly anomeric spiroketal core is a notable subunit in the natural product’s structure. We report a rapid and convergent approach to the spiroketal group, resulting in the formation of two isomeric singly anomeric spiroketals. We describe the origin of this rarely described outcome in spirocycle formation and subsequently propose a correction to a stereocenter in the natural product.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03751