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Complete assignment of the 1H and 13C NMR spectra of 8-hydroxy-7-methoxy-4-methyl-1α,4α,4aα,8β,8aα-tetrahydro-1,4-methanonaphthalen-5(1H)-one

✍ Scribed by David E. Minter; Alar P. Marchand; Shao-Po Lu

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
380 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Diels–Alder cycloaddition of a mixture of 1‐ and 2‐methylcyclopentadienes (1a and 1b, respectively) to 2‐methoxy‐p‐benzoquinone (2) gave a mixture of isomeric endo [4 + 2] cycloadducts (3a–3d). Fractional recrystallization of this product mixture from EtOAc‐hexane gave 6‐methoxy‐1‐methyl‐1α,4α,4aα,8aα‐tetrahydro‐1,4‐methanonaphthalene‐5,8‐dione (3a). Reaction of 3a with NaBH~4~ in the presence of cerium(III) chloride resulted in the selective reduction of the less hindered CO group in 3a, thereby affording 8‐hydroxy‐7‐methoxy‐4‐methyl‐1α,4α,4aα,8β,8aα‐tetrahydro‐1,4‐methanonaphthalen‐5(1__H__)‐one (4). The ^1^H and ^13^C NMR spectra of 4, a novel tricyclic ketoalcohol, have been completely assigned by using a combination of one‐ and two‐dimensional NMR techniques.

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