An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors.
Dihydroxyalkenes or their monoprotected alcohol derivatives are transformed to 5,5- and 5,6-spiroketals through a sequence involving an initial iodocyclization, followed by a silver triflate mediated spiroketalization step on the derived hydroxy-iodoether.
Tony
K A
KA
Department of Chemistry, Hunter College/CUNY, New York, NY 10021, USA.
Li
Xiaohua
X
Dabideen
Darrin
D
Li
Jialiang
J
Mootoo
David R
DR
D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D003516:Cycloparaffins; D004987:Ethers; D005663:Furans; D006847:Hydrocarbons, Iodinated; D013141:Spiro Compounds; C520774:spiroketal