Phenol oxidation and biosynthesis. Part XXIV. Origin of chirality in the erythrinan system and derivation of the lactone rings of α- and β-erythroidine
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2278-2283
- https://doi.org/10.1039/p19740002278
Abstract
Erysodienone (III) has been resolved, and the laevorotatory (5S)-antipode is shown to be the precursor of the Erythrina alkaloids. Chiral 5,6,8,9-tetrahydro-2,12-dimethoxy-7H-dibenz[d,f]azonine-3,11-diol, derived from resolved erysodienone, is optically unstable at 20 and at 0°. The biosynthetic implications are discussed. The aromatic Erythrina alkaloids are shown to be specifically incorporated into the lactone erythroidine alkaloids with retention of the 17-hydrogen atom. Cleavage of the aromatic ring in nature is discussed.Keywords
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