Synthesis of Vinca Alkaloids and Related Compounds, XXII. Some Chemical Transformations of 15‐Oxovincamone | Zendy

Sápi János | Zendy; Szabó Lajos | Zendy; BaitzGács Eszter | Zendy; Kalaus György | Zendy; Szántay Csaba | Zendy; KarsaiBihátsi ÉVa | Zendy

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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.

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