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  • Title: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the CD-spiroacetal segment.
    Author: Paterson I, Coster MJ, Chen DY, Gibson KR, Wallace DJ.
    Journal: Org Biomol Chem; 2005 Jul 07; 3(13):2410-9. PubMed ID: 15976858.
    Abstract:
    Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 , relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60 : 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal by acid-promoted equilibration, chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of , thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series.
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