Highly efficient and mild cascade reactions triggered by bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate and a concise total synthesis of camptothecin.
A mild and efficient cascade methodology is reported to construct variously substituted indolizino[1,2-b]quinolin-9(11H)-ones. Efficiently triggered by bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate under mild conditions, this cascade achieved significant enhancements in chemical yields. Utilizing this highly efficient domino reaction followed by a Sharpless dihydroxylation, an eight-step total synthesis of camptothecin was accomplished from a known pyridine derivative in direct fashion with an overall yield of 47% and 95% ee.
Zhou
Hai-Bin
HB
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.
Liu
Guan-Sai
GS
Yao
Zhu-Jun
ZJ
D002166:Camptothecin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry
D008698:Mesylates; D009943:Organophosphorus Compounds; D011725:Pyridines; C494538:bis(triphenyl) oxodiphosphonium trifluoromethanesulfonate; C023666:pyridine; D002166:Camptothecin