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Consequences of acid catalysis in concurrent ring opening and halogenation of spiroketals
T G LaCour1, Z Tong, P L Fuchs
1Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA. lacour@purdue.edu
Organic Letters
|June 3, 2000
Abstract:
[formula: see text] Lewis and/or Bronsted acid additives permit ring opening and halogenation of spiroketals at substantially reduced temperatures to produce omega-iodo enol ethers in improved yield and purity, which can undergo further reaction in the presence of distal electrophilic centers to give new steroid skeletons.