Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 570-577Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.66
Keywords
alkynes; cyclocondensation; cycloisomerization; gold-catalyzed; 5,5-spiroketals
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Funding
- National Science Foundation [NSF-CHE 0749918]
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A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catalysis in the activation of alkyne p-systems.
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