PHOTOINDUCED VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT (PHOTO-VCP-CP) - A METHODOLOGY FOR CHIRAL BICYCLO[3.2.0]HEPTENES AND THEIR APPLICATION IN NATURAL PRODUCT SYNTHESES

Authors
SONAWANE HR BELLUR NS KULKARNI DG AHUJA JR
Citation
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
Citations number
59
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
12
Year of publication
1993
Pages
875 - 884
Database
ISI
SICI code
0936-5214(1993):12<875:PVR(>2.0.ZU;2-G
Abstract
(+)-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.