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Zur Struktur des Sikkimotoxins I. Synthese von stereoisomeren 6,7‐Dimethoxy‐Analogen des Podophyllotoxins. 11. Mitteilung über mitosehemmende Naturstoffe
Author(s) -
Schreier E.
Publication year - 1963
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19630460110
Subject(s) - chemistry , stereochemistry , absolute configuration , podophyllotoxin , total synthesis , podophyllum , derivative (finance) , natural product , financial economics , economics
The total synthesis of several stereoisomeric 6,7‐dimethoxy‐analogues of podo‐phyllotoxin, the main component of the resin of Podophyllum elvzodi and P. peltatunt is described. One of the synthetic lactones, for which the name of picrosikkimotoxin is proposed, corresponds in its configuration to picropodophyllin, the compound produced from podophyllotoxin by base‐catalysed epimerisation. The structure corresponding to the synthetic picrosikkimotoxin has been assigned by CHATTERJEE and coworkers to the so called isosikkimotoxin, the product of the base‐catalysed epimerisation of sikkimotoxin, a new lignan lacton isolated in 1950 by the Indian group from the rhizomes of Podoflhyllurn sikkinzensis R. C HATTERJEE et M UCKERJEE , and thought to be analogous to podophyllotoxin. The properties of the synthetic, optically active picrosikkimotoxin, the structure and absolute configuration of which have been established unequivocally by stereochemical correlation with picropodophyllin, and of its acetyl derivative do not agree in all respects with published data for isosikkimotoxin and acetylisosikkimotoxin. This fact gives rise to some doubt as to the correctness of the proposed structure or the purity of the compounds from natural source. A direct comparison of the synthetic and natural compounds has not been possible, due to the unavailability of authentic material.