TY - JOUR
T1 - Studies on epoxides-V. Reactions with 5,6-epoxy-eudesman-8β,12-olides
AU - Vita-Finzi, P.
AU - Kashman, Y.
AU - Glotter, E.
AU - Lavie, D.
N1 - Funding Information:
Acknowledgement--One of us (P.V.F.) thanks the Consiglio Nazionale delle Ricerche, Italy, for a Research Fellowship. We are indebted to “Plantex” Ltd., Nathania for a generous supply of lnulo heleniume xtracts used as starting material.
PY - 1968
Y1 - 1968
N2 - The acid catalysed opening of the epoxide ring in several 5,6-epoxy-eudesman-8β,12-olides has been analysed. Treatment of the α-oriented epoxides XI and XIVb with HBr results in the formation of the diols XIX and XXI, whereas the β-epoxide XIII yields the expected trans diequatorial bromohydrin XXVId. The above and some other related reactions of eudesm-5-en-8β,12-olides with osmium tetroxide are described. An internal displacement of the epoxide ring in the epoxy-lactone XVI to yield the hydroxy-lactone XXVII takes place under mild alkaline conditions.
AB - The acid catalysed opening of the epoxide ring in several 5,6-epoxy-eudesman-8β,12-olides has been analysed. Treatment of the α-oriented epoxides XI and XIVb with HBr results in the formation of the diols XIX and XXI, whereas the β-epoxide XIII yields the expected trans diequatorial bromohydrin XXVId. The above and some other related reactions of eudesm-5-en-8β,12-olides with osmium tetroxide are described. An internal displacement of the epoxide ring in the epoxy-lactone XVI to yield the hydroxy-lactone XXVII takes place under mild alkaline conditions.
UR - http://www.scopus.com/inward/record.url?scp=49949131205&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)96315-X
DO - 10.1016/S0040-4020(01)96315-X
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AN - SCOPUS:49949131205
SN - 0040-4020
VL - 24
SP - 5847
EP - 5859
JO - Tetrahedron
JF - Tetrahedron
IS - 17
ER -