Synthesis of vinca alakaloids and realated compounds 98. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7S,20S)‐(+)‐rhazidigenine and (2R,7S,20S)‐(+)‐rhazidine |
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| Authors: | Jnos les Gyrgy Kalaus Lajos Szab
Albert Lvai Istvn Greiner Mria Kajtr‐Peredy Pl Szab
Csaba Szntay |
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| Institution: | János Éles,György Kalaus,Lajos SzabÓ,Albert LÉvai,IstvÁn Greiner,MÁria KajtÁr‐Peredy,PÁl SzabÓ,Csaba SzÁntay |
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| Abstract: | The oxidation of (‐)‐tabersonine ( 1 ) with dimethyldioxirane (DMD) in neutral and acidic medium gave 16‐hydroxytabersonine‐N‐oxide ( 3 ) and the didehydrovincamine isomers 4 and 5 , respectively. (+)‐14,15‐Didehydro‐quebrachamine ( 7 ) furnished the hydroxyindolenine 9 , and the pentacyclic derivative 11 . (+)‐Quebrachamine ( 8 ) and DMD in neutral medium gave (7S,20S)‐(+)‐rhazidigenine ( 12 ) which was converted to (2R,7S,20S)‐(+)‐rhazidine ( 13b ) with hydrochloric acid. |
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