1295471-53-2Relevant academic research and scientific papers
Total synthesis of pactamycin and pactamycate: A detailed account
Hanessian, Stephen,Vakiti, Ramkrishna Reddy,Dorich, Stéphane,Banerjee, Shyamapada,Deschênes-Simard, Beno?t
, p. 9458 - 9472 (2013/01/15)
This article describes synthetic studies that culminated in the first total synthesis of pactamycin and pactamycate and, in parallel, the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate, lacking the 6-methylsalicylyl moiety. Starting with l-threonine as a chiron, a series of stereocontrolled condensations led to a key cyclopentenone harboring a spirocyclic oxazoline. A series of systematic functionalizations led initially to the incorrect cyclopentanone epoxide, which was "inverted" under solvolytic conditions. Installation of the remaining groups and manipulation of the oxazoline eventually led to pactamycin, pactamycate, and their desalicylyl analogues.
Total synthesis of pactamycin
Hanessian, Stephen,Vakiti, Ramkrishna Reddy,Dorich, Stephane,Banerjee, Shyamapada,Lecomte, Fabien,DelValle, Juan R.,Zhang, Jianbin,Deschenes-Simard, Benoait
supporting information; experimental part, p. 3497 - 3500 (2011/05/12)
Lest we forget: 50 years after pactamycin was first isolated from a fermentation broth of Streptomyces pactum var pactum, this highly functionalized aminocyclopentitol natural product has finally succumbed to total synthesis. The modular and stereocontrolled introduction of functional groups should lead to the synthesis of less toxic congeners that maintain the antibacterial and cytotoxic activities. Copyright
