Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Diterpenoids. XX. Nitration of Dimethyl 1, 2, 3, 10-Tetrahydro-4β, 10α-dimethyl-4H-fluorene-4α, 6-dicarboxylate and Its Hydrogenated Stereoisomers
AKIRA TAHARAYASUO OHTSUKA
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1972 Volume 20 Issue 8 Pages 1637-1647

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Abstract
Dimethyl 1, 2, 3, 10-tetrahydro-4β, 10α-dimethyl-4H-fluorene-4α, 6-dicarboxylate and its hydrogenated stereoisomers were nitrated with conc. HNO3-Ac2O to give mononitro compound as a single product. Namely, ⊿5-diester (X) was nitrated to give only 12-nitro compound (XI) and, in contrast, four possible stereoisomers due to the asymmetric centers at C-5 and C-6 of the saturated diester (XVII, XVIII, XIX, and XX) gave only 13-nitro compounds (XXI, XXII, XXIII, and XIV, respectively). Accordingly, 12-and 13-substituted (NO2, NH2, OH, and OMe) compound could be optionally obtained herein.
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© The Pharmaceutical Society of Japan
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