Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 1, Pages 297-304Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002501
Keywords
hydrogen bonds; natural products; spirofungins; spiroketals; total synthesis
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Funding
- Australian Research Council [DP0770408]
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The stereoselective total synthesis of the spiroketal containing Streptomyces metabolite (-)-spirofungin A (1) is described. A key step involved a spiroketalisation controlled by an intramolecular H-bond which favoured the desired spiroketal 4 (13:1 ratio). The presence of the intramolecular H-bond in 4 is possibly due to a 1,5-alkyne-oxygen interaction. Other key steps include an efficient cross-metathesis to form the spiroketal precursor, a tin mediated syn-aldol reaction and a Stille cross-coupling reaction to create the C22-C23 bond. A final Wittig extension followed by deprotection gave (-)-spirofungin A (1).
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