Barrero Alejandro F, Arseniyadis Siméon, Quílez del Moral José F, Herrador M Mar, Valdivia M, Jiménez D
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Avda. Fuentenueva s/n, 18071 Granada, Spain.
J Org Chem. 2002 Apr 19;67(8):2501-8. doi: 10.1021/jo0161882.
The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(II), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.
以二萜反式-communic酸为起始原料合成杀菌剂二氢猕猴桃内酯C，总产率为11.7%。该过程的关键步骤是由Pd(II)催化的新的双内酯化反应，该反应从降蒈二烯二酸生成足叶草内酯型四环骨架。我们还对不同天然足叶草内酯及其合成前体的结构-生物活性进行了研究。因此，在C-17位具有醚型取代基的二烯二内酯中发现了最高的细胞毒性活性，而γ-内酯环的闭合对于呈现最大抗菌活性并不关键。
