A new taxane derivative from the heartwood of Taxus mairei

Phytochemistry
1988.0

Abstract

The one-proton doublets at δ 6.11 and 5.90 were attributed to H-10 and H-9 (J₉,₁₀ = 10.7 Hz). A one-proton double double doublet at δ 2.75 was assigned to H-14β [4]. Irradiation of the H-14β resulted in the collapse of the triplet at δ 5.76 of H-13 into a broad singlet. Two broad singlets at δ 5.30 and 4.91 for the H-16 and H-16' protons collapsed into two singlets when the long range couplings (H-5 with H-16 and H-5 with H-16') were removed by irradiating at δ 5.54 of H-5. A one-proton doublet at δ 3.10 was assigned to H-3 [3, 4]. Four three-proton singlets at δ 2.23, 1.60, 1.06 and 0.76 were attributed to the methyls at C-12, C-15, C-15' and C-8, respectively. Moreover, DEPT and ¹³C NMR spectra also confirmed the structure for 1, showing signals of seven primary carbons (-Me), five secondary carbons (≥CH₂), 13 tertiary carbons (≥CH) and 10 quaternary carbons (≥C<). In order to confirm the stereochemistry of 1, a NOESY experiment was conducted. The NOESY spectrum (Fig 1) showed 14 cross peaks and is listed in Table 1. The cross peak 5 belonged to the NOE signal of Me-15' with H-13, and this indicated the β-position of H-13. The presence of a cinnamate group at the α-position of C-5 was shown by the cross peaks 9 and 11. Furthermore, cross peaks 6 and 8 confirmed that C-9 and C-10 both had an acetate group at the α- and β-position, respectively. The absolute configuration of 1 was not established. However, on the basis of the results presented above, structure 1 is assigned and the compound is 9α,10β,13α-triacetoxy-5α-cinnamoyoxytaxa-4(20),11diene which has not been reported previously.

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