In this report, we describe the synthesis and full spectroscopic characterization of a previously unreported podophyllotoxin (PTOX) analogue bearing a second 3,4,5-trimethoxyphenyl (TMP) unit at the C-4 position through an ester linkage. This dual-TMP PTOX derivative is obtained from a brominated PTOX intermediate. In this precursor, the bromine atom is located on the TMP aromatic ring at the 2′-position. The new compound was fully characterized by proton (1H), carbon-13 (13C), heteronuclear single-quantum coherence (HSQC), and distortionless enhancement by polarization transfer (DEPT) NMR spectroscopy. Ultraviolet–visible (UV-Vis) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, mass spectrometry and elemental analysis were also performed to confirm the structure and purity of the synthesized ester derivative.
(5R,5aR,8aR,9S)-9-(2-Bromo-3,4,5-trimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-5-yl 3,4,5-trimethoxybenzoate
Gianoncelli, Alessandra;Khan, Imran;Ribaudo, Giovanni
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2026-01-01
Abstract
In this report, we describe the synthesis and full spectroscopic characterization of a previously unreported podophyllotoxin (PTOX) analogue bearing a second 3,4,5-trimethoxyphenyl (TMP) unit at the C-4 position through an ester linkage. This dual-TMP PTOX derivative is obtained from a brominated PTOX intermediate. In this precursor, the bromine atom is located on the TMP aromatic ring at the 2′-position. The new compound was fully characterized by proton (1H), carbon-13 (13C), heteronuclear single-quantum coherence (HSQC), and distortionless enhancement by polarization transfer (DEPT) NMR spectroscopy. Ultraviolet–visible (UV-Vis) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, mass spectrometry and elemental analysis were also performed to confirm the structure and purity of the synthesized ester derivative.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
