Tetrahedron p. 10867 - 10878 (1994)
Update date:2022-08-04
Topics:
Fitjer, Lutz
Kanschik, Andreas
Majewski, Marita
The dispiroketones 4-6 have been synthesized and rearranged by treatment with acids yielding the bicyclic enone 36 under kinetic control and the <3.3.3>propellane 37 under thermodynamic control.The corresponding alcohols 10-12 all yield the <3.3.3>propellane 41.The rearrangement of <7,7-D2>-12 to <8,8-D2>-41 proceeds stereospecifically and points to dispirane 42 as potential precursor of(+/-)modhephene 43.Likewise, dispiranes 44 and 46 are potential precursors of (+/-)-isocomene 45.
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Doi:10.1016/0022-1139(94)03079-0
(1994)Doi:10.1021/ol901455q
(2009)Doi:10.1002/adsc.201300703
(2014)Doi:10.1021/jo01287a068
(1967)Doi:10.1021/jo5004168
(2014)Doi:10.1021/ma500606e
(2014)
