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The constitution and stereochemistry of ε-caesalpin

✍ Scribed by A. Balmain; K. Bj»mer; J.D. Connolly; G. Ferguson

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
203 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

The isolation 1,2 and structural eluoidation20f a-, $-, y-and Ocaesalpins from the seeds of Coesrloinia bonduoella have been reported. We have isolated, from the same source, 8 new crystalline compound, s-csesalpin, which is assigned structure(I)(or enantiomer) on chemical and SpeCtrOScOpic evidence. This is confirmed by an X-ray analysis of the p-bromobenzoste(II)which, in addition, establishes the stereochemistry at the remaining asymmetric centres and the absolute configuration as in(III). c-Caesslpin C24H3407, m.p. 191-194', [al, +2', shows in its n.m.r. spectrum a 2,3 disubstituted furan ring [H-16, v 2*77; H-15, v 3*61; both doublets, J = 2 c./sec.], two secondary acetates [v 8*10, 7.94 (2Cg3COO-); 4*76, doublet and 4.7, multiplet (2%gOAc)1 8nd four tertisryc-methyl

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