Synthesis of anti- and syn-diol epoxides of trans-3,4-dihydroxy-3,4- dihydrobenzo[ghi] fluoranthene: Model planar diol epoxides
Date of Original Version
We describe the preparation of anti- and syn-3,4-dihydroxy-5,5a-epoxy- 3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene (2 and 3) as model planar diol epoxides. These compounds were synthesized by a dihydroarene method in 10 steps starting from 4H-cyclopenta[def]phenanthrene. These are the first examples of diol epoxides in which a five-membered ring is fused to the saturated ring bearing an epoxide group, and they are the rigid analogues of the extensively studied benzo[c]phenanthrene diol epoxides (5 and 6). In accord with expectation, 1H NMR data indicated that the diol conformations of 2 and 3 are locked into diequatorial and diaxial conformations, respectively, and thus are suitable for comparative DNA binding studies.
Journal of Organic Chemistry
Chang, Hui-Fang, and Bongsup P. Cho. "Synthesis of anti- and syn-diol epoxides of trans-3,4-dihydroxy-3,4- dihydrobenzo[ghi] fluoranthene: Model planar diol epoxides." Journal of Organic Chemistry 64, 25 (1999): 9051-9056. doi:10.1021/jo9907944.