PHOTOINDUCED VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT (PHOTO-VCP-CP) - A METHODOLOGY FOR CHIRAL BICYCLO[3.2.0]HEPTENES AND THEIR APPLICATION IN NATURAL PRODUCT SYNTHESES
Hr. Sonawane et al., PHOTOINDUCED VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT (PHOTO-VCP-CP) - A METHODOLOGY FOR CHIRAL BICYCLO[3.2.0]HEPTENES AND THEIR APPLICATION IN NATURAL PRODUCT SYNTHESES, Synlett, (12), 1993, pp. 875-884
(+)-DELTA3-Carene serves as a useful source material in generating chi
ral bicyclo[3.2.0]heptenes on a preparative scale employing photochemi
cal vinylcyclopropane-cyclopentene rearrangement as a convenient metho
d. These chiral units are useful as key intermediates in asymmetric sy
nthesis of different natural products known for significant biological
activity. Adaptation of spirocyclic VCP-CP - oxidative scission seque
nce provides a short way for a three carbon intercalation of cycloalka
nones to cyclic 1,5-diones. The potential of this sequence in the synt
hesis of some important carbon frameworks is highlighted.