Deacetylation of paclitaxel and other taxanes

An Efficient Semi‐Synthetic Method to Construct Docetaxel via Sterically Crowded Linear Side Chain Esterification

“…Compound 15 was obtained in 89% yield. [13] Thus, four steps synthetic route provided docetaxel in 51% overall yield, of which, the optical rotation was [14] In order to improve the synthetic efficiency, by-product 13 can be reused. ), H 2 O 2 in THF afforded docetaxol (1) in 93% yield.…”

The Reductive Fragmentation of 7‐Hydroxy‐9,10‐dioxotaxoids

“…The L‐selectride reductive fragmentation could also be carried out on 2′‐protected 9,10‐dioxotaxanes bearing amino acidic side chains, as exemplified by the conversion of cephalomannine ( 14a ),27 a side product of the isolation of Taxol, into its corresponding C‐ seco ‐taxane 15 (Scheme ). After chemoselective deacetylation of the 10‐hydroxy group,28 the 2′‐hydroxy group was protected as a TES ether, and the α‐ketol system was subjected to autoxidation conditions in the presence of Cu(OAc) 2 . The reductive fragmentation was then uneventful, affording, after deprotection, 15 in overall 21% yield from 14a .…”

Stereochemical differentiation of C‐7 hydroxyltaxane isomers by electrospray ionization mass spectrometry

“…2a was synthesized from 10‐deacetylpaclitaxel by esterification of the C‐2′ and C‐10 hydroxyl groups with propionic anhydride in anhydrous tetrahydrofuran (THF), followed by selective deacylation of the C‐2′ acyl group with H 2 O 2 and sodium bicarbonate according to a previously reported scheme 36…”