P. Joseph-Nathan, M. Meléndez Rodríguez, C. M. Cerda-García-Rojas, C. A. N. Catalán Photochemical rearrangements of highly functionalized longipinene derivatives Tetrahedron Letters, Volume 37, Issue 45, 4 November 1996, Pages 8093-8096. ISSSNI:0040-4039 DOI: http://dx.doi.org/10.1016/0040-4039(96)01848-5
Ultraviolet irradiation of 7?,9?-diacetyloxylongipin-2-en-1-one (3) affords the vulgarone A derivative 5 and compound 7 which possesses a novel tricyclic sesquiterpene skeleton named pingilonane. The photorearrangements of 3 occur via [1,3] sigmatropic shifts of the C4?C10 or of the C4?C5 bond, respectively. Similarly, irradiation of 7?,8?,9?-triacetyloxylongipin-2-en-1-one (4) affords 6 and 8. Some biogenetic implications of these transformations are discussed.
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