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Synthesis of Vinca Alkaloids and Related Compounds, XXII. Some Chemical Transformations of 15‐Oxovincamone
Author(s) -
Sápi János,
Szabó Lajos,
BaitzGács Eszter,
Kalaus György,
Szántay Csaba,
KarsaiBihátsi ÉVa
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519850907
Subject(s) - sodium methoxide , chemistry , racemization , epimer , vinca , methoxide , hydrolysis , organic chemistry , vindoline , solvolysis , alkaline hydrolysis , stereochemistry , methanol , medicine , botany , surgery , chemotherapy , vinblastine , biology
In the course of an attempted synthesis of E ‐norvincamine ( 4 ) (−)‐15‐oxovincamone ( 7 ), prepared from (−)‐vincamone ( 2 ), was converted by means of methanolic sodium methoxide to give the (−)‐ 11 ‐ cis and (±)‐ 12 ‐ trans alcohols. Alkaline hydrolysis of the dioxo compound 7 furnishes the α‐oxo acids 8 and 9 as a result of an epimerization‐racemization process.