Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 24, Pages 7452-7466Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102462
Keywords
alkenes; bistramide A; protein kinase C; total synthesis
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Funding
- European Commission [LSHB-CT-2004-503467]
- Ministere de la Recherche et de la Technologie
- Medical Research Council [G9818340B] Funding Source: researchfish
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The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product.
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