Synthesis of the C16−C28 Spiroketal Subunit of Spongistatin 1 (Altohyrtin A):  The Pyrone Approach

Synthesis of the C16−C28 Spiroketal Subunit of Spongistatin 1 (Altohyrtin A):  The Pyrone Approach

The synthesis of the CD spiroketal fragment of spongistatin 1 (altohyrtin A) has been accomplished utilizing the addition of a metalated pyrone to an aldehyde and subsequent acid-catalyzed spirocyclization. A stereoselective hydrogenation and subsequent conformational inversion establish the C19 ste...

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Veröffentlicht in:Organic letters 2000-04, Vol.2 (7), p.957-960
Hauptverfasser: Crimmins, Michael T, Katz, Jason D
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Antineoplastic Agents - chemical synthesis
Cyclization
Ethers, Cyclic - chemical synthesis
Lactones - chemical synthesis
Macrolides
Molecular Conformation
Pyrones - chemistry
Stereoisomerism
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Zusammenfassung:The synthesis of the CD spiroketal fragment of spongistatin 1 (altohyrtin A) has been accomplished utilizing the addition of a metalated pyrone to an aldehyde and subsequent acid-catalyzed spirocyclization. A stereoselective hydrogenation and subsequent conformational inversion establish the C19 stereocenter and the axial−equatorial spiroketal center.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005605e