Journal of Organic Chemistry p. 4251 - 4256 (1983)
Update date:2022-08-03
Topics:
Wilton, John H.
Doskotch, Raymond W.
A comparison was made of the products generated from lipiferolide (2) upon treatment with SOCl2, HCl, and BF3*Et2O.SOCl2 formed three epoxide-opened compounds, chlorhydrin 3 and two allylic alcohols, 4 and 5, three cyclization products of the guaianolide type, chloro compound 9 and olefins 1 and 10, as well as three novel bicyclo<6.2.0>decanes, 6, 7, and 8.HCl generated the epoxide-opened substances 3, 4, and 5 and guaianolides 1, 9, and 10, but no cyclobutane products.BF3*Et2O gave fluorohydrin 11 as the major component and ketone 12, xanthanolide 13, and epitulipinolide (4,5-deoxylipiferolide) as compounds not observed from the other reagents, along with small yields of allylic alcohol 4 and guaianolides 1 and 10.
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