Rearrangement of O-Cinnamoyltaxicin I to a Novel C-13 Spiro-Taxane

E.L.M. van Rozendaal, H. Veldhuis, B. van Veldhuizen, T.A. van Beek, Æ. de Groot, P.H. Beusker, H.W. Scheeren

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Abstract

During the large-scale synthesis of an O-cinnamoyltaxicin I acetonide, an intermediate for the semisynthesis of 7-deoxypaclitaxel derivatives, side-product 3 was formed via a vinylogous retro-aldol reaction and a long-range hydride shift from O-cinnamoyltaxicin I (1) under alkaline reaction conditions. Compound 3 has two hemi-acetal bridges at C-1,C-9 and C-10,C-13. Compound 4 was formed from side-product 3 under acidic reaction conditions and is the first C-13 spiro-taxane described in the literature. This spiro-taxane has two acetal bridges between C-1,C-13 and C-10,C-13.
Original languageEnglish
Pages (from-to)179-181
JournalJournal of Natural Products
Volume63
DOIs
Publication statusPublished - 2000

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    van Rozendaal, E. L. M., Veldhuis, H., van Veldhuizen, B., van Beek, T. A., de Groot, Æ., Beusker, P. H., & Scheeren, H. W. (2000). Rearrangement of O-Cinnamoyltaxicin I to a Novel C-13 Spiro-Taxane. Journal of Natural Products, 63, 179-181. https://doi.org/10.1021/np990206h