Application of Pd(0)-catalyzed intramolecular oxazine formation to the efficient total synthesis of (-)-anisomycin.
The enantioselective total synthesis of (-)-anisomycin, a potent antibiotic agent, has been achieved. The key steps are a Pd(0)-catalyzed stereoselective intramolecular oxazine formation from d-tyrosine and pyrrolidine formation by catalytic hydrogenation of the oxazine.
Joo
Jae-Eun
JE
College of Pharmacy, SungKyunKwan University, Suwon 440-746, Korea.
Lee
Kee-Young
KY
Pham
Van-Thoai
VT
Tian
Yong-Shou
YS
Ham
Won-Hun
WH
D000841:Anisomycin / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D014443:Tyrosine / Q000737:chemistry
D000900:Anti-Bacterial Agents; D010078:Oxazines; D011759:Pyrrolidines; D014443:Tyrosine; D010165:Palladium; D000841:Anisomycin