Studies toward the total synthesis of diterpene antibiotic guanacastepene A: construction of the hydroazulenic core.
[reaction: see text] As a part of studies aimed toward the total synthesis of biologically important natural product guanacastepene A of contemporary interest, a new and concise route to a fully functionally endowed hydroazulenic core is delineated. The strategy involves the building of the requisite stereochemical features on a endo-tricyclo[5.2.1.0(2,6)]decane matrix and excision of the five-membered ring through a retro-Diels-Alder reaction. Generation of the seven-membered ring to access the hydroazulenic framework was achieved employing ring closure metathesis (RCM) reaction as the key step.
Mehta
Goverdhan
G
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. gm@orgchem.iisc.ernet.in
Umarye
Jayant D
JD
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D000900:Anti-Bacterial Agents; D003517:Cyclopentanes; D004224:Diterpenes; D007202:Indicators and Reagents; C454620:guanacastepene A