The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the CD-spiroacetal segment |
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Authors: | Paterson Ian Coster Mark J Chen David Y-K Gibson Karl R Wallace Debra J |
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Affiliation: | University Chemical Laboratory, Lensfield Road, University of Cambridge, Cambridge, UKCB2 1EW. ip100@cam.ac.uk |
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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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