Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation.
The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains.
Perepogu
Arun Kumar
AK
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500 607, Andhra Pradesh, India. aruniict@gmail.com
Raman
D
D
Murty
U S N
US
Rao
Vaidya Jayathirtha
VJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism
C540870:5-hydroxy-9-methyl-6-nonen-9-olide; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006573:Heterocyclic Compounds, 1-Ring; D007783:Lactones; D018942:Macrolides; C527511:stagonolide