5'-Nor anhydrovinblastine

Novel antitumor agents from higher plants

“…6,7 In this compound, the 9-membered C ring of 1 has been replaced by an 8-membered ring via a Polonovski Type-B fragmentation and reclosure, while the D ring has undergone dehydration. 6,8,9 Wani et al in 1971, 10 has a unique mode of action (it acts as a mitotic inhibitor by promoting the assembly of microtubules) and is used to treat breast and ovarian cancer. [11][12][13] Although this compound is an exciting chemotherapeutic agent, supply problems were an early obstacle in its development and prompted extensive semi-and total-synthetic efforts.…”

“…[14][15][16] The former led to the synthesis of Taxotere (6) from the more readily available, 10-deacetyl-baccatin III 7), a compound isolated from the needles of the European yew tree (Taxus baccata L.). 17 The natural alkaloid camptothecin (8) isolated from the Chinese tree Camptotheca acuminata 18 is another compound that has undergone continual structural modification aimed at developing more useful chemotherapeutic agents. It is used to treat gastric, rectal, colon, and bladder cancers, but has limited natural availability and is poorly water soluble.…”

Reactivity of Vinca alkaloids in superacid

“…Vinflunine 3a can be prepared directly from vinorelbine 2a but more efficiently by fluorination of anhydrovinblastine 2b followed by C 0 -ring contraction [11].…”

Characterization of impurities in semi-synthetic vinorelbine bitartrate by HPLC-MS with mass spectrometric shift technique

“…Vinorelbine, first prepared and characterized in 1979 by Potier and co-workers [1], has been demonstrated significant clinical activities against nonsmall cell lung cancer, bronchial, adenocarcinoma, breast cancer, and head/neck squamous cell carcinoma. Moreover, it has been widely employed in combination with cisplatinum with or without 5-fluorouracil for the treatment of lung cancer and head/neck carcinomas [2,3].…”