Tetrahedron Letters p. 2227 - 2230 (1994)
Update date:2022-08-04
Topics:
Hauke
Hauke, Verena
Trendel
Trendel, Jean M.
Albrecht
Albrecht, Pierre
Connan
Connan, Jacques
Acidic K-10 montmorillonite clay-catalysed rearrangement of hop-22(29)-ene 5 and of hop-17(21)-ene 6 leads to the formation of small quantities of various fernenes and of new compounds, the 14-methyl-13,15-cyclo-B':A'-neo-26-nor-14,15-seco-18α-gammacer-7-ene 8 and its Δ8- and Δ9((11))-isomers 9 and 10, the structures of which have been established by MS and NMR spectroscopy. This novel hopane skeleton transposition also operates on bacterial sedimentary hopenes, as shown by GC-MS investigations of the alkene fraction from a recent lacustrine sediment.
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(1987)
