Utilization of selenium-directed [2 + 2] cycloadditions: concise synthesis of (±)-fragranol
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 695-700
- https://doi.org/10.1039/p19940000695
Abstract
The reaction of 2-(phenylseleno)prop-1ene 1 and methyl vinyl ketone 2 in the presence of EtAlCl2 gave the [2 + 2] cycloadducts 3a and 3b. A radical substitution of the adducts 3a and 3b with allytributyltin gave the allylated cyclobutane product, which was transformed into the cyclobutane natural product, (±)-fragranol. Stereoselective radical substitution using the ethylene glycol ketals of compounds 3a and 3b was also achieved.Keywords
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