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Synfacts 2005(0): 0004-0004
DOI: 10.1055/s-2005-865344
DOI: 10.1055/s-2005-865344
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of (+)-Leucascandrolide A
Contributor(s): Philip KocienskiQ. Su, J. S. Panek*
Boston University, USA
Total Synthesis of (+)-Leucascandrolide A
Angew. Chem. Int. Ed. 2005, 44: 1223-1225
Boston University, USA
Total Synthesis of (+)-Leucascandrolide A
Angew. Chem. Int. Ed. 2005, 44: 1223-1225
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
tetrahydropyrans - heteroannulation - allylsilanes
Significance
Leucascandrolide A (from a calcareous sponge Leucascandra caveolata) is cytotoxic towards various cancer cells and it inhibits the pathogenic yeast Candida albicans. It is probably a metabolite of opportunistic bacteria.
Comment
The cis- and trans-2,6-disubstituted tetrahydropyran rings A and B of the target were constructed using an intramolecular sila-Prins-type cyclization. The diastereoselectivity of the cyclization was controlled by steric and electronic effects in the homochiral allylsilane and crotylsilane.