Seco-taxane

Taraboletti G, Gatto C, Riva A, et al. Anti-Angiogenic and Anti-Metastatic Activity of IDN 5390, a New C-Seco Taxane Derivative. Proceedings of the AACR, Vol. 42, March 2001. abstract 3162. 

Total synthesis of A-seco taxane was accomplished using aldol condensation route using Yb triflate as the catalyst [155],... 

Under oxidizing conditions (Jones reagent), taxol is converted to the 7-keto derivatives 20a and 20b (43) (see Scheme 3). Under these same conditions (2,11,28), the free 13-hydroxyl group of baccatin III (13b) and 10-deacetyl baccatin III (13a) is oxidized to form 13-oxobaccatin III (21b) and the deacetyl derivative (21a), respectively. Treatment of compound 20c, derived from the oxidation product 20a after protection of its 2 -hydroxyl group, with base leads to rearrangement products such as D-seco taxane 22. 

Ferlini, C., Raspaglio, G., Mozzetti, S., et al. (2005) The seco-taxane IDN5390 is able to target class III P-tubulin and to overcome paclitaxel resistance. Cancer Research, 65, 2397-2405. 

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