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13C NMR spectrum. We concluded that the new peak corresponded to a C34 epimer of 14 (ent-1). Epimerization of C34 has previously been reported to occur under basic conditions (see ref 17).
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54
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0041769131
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note
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6 Both of our samples of 1 and 14, for which the optical rotation data are reported, gave single peaks by chiral HPLC under the conditions given above (see ref 15).
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55
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0343632337
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It has previously been observed that the optical rotation value of acetogenins is largely due to the stereochemistry of the butenolide and, to a lesser extent, due to the stereochemistry of the THF diol portion: Duret, P.; Figadère. B.: Hocquemiller, R.; Cavé, A. Tetrahedron Lett. 1997, 38, 8849-8852.
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