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Author(s) -
Zampella Angela,
Bassarello Carla,
Bifulco Giuseppe,
GomezPaloma Luigi,
D'Auria Maria Valeria
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:5<749::aid-ejoc749>3.0.co;2-n
Subject(s) - chemistry , stereochemistry , depolymerization , sponge , cover (algebra) , stereoselectivity , organic chemistry , botany , catalysis , mechanical engineering , engineering , biology
The cover picture shows the structure of reidispongiolide A (center), a representative of a macrolide family isolated from the New Caledonian sponges Neosiphonia superstes and Reidispongia coerulea. As shown at the bottom of the picture, its potent antiproliferative activity can be explained as being due to the interaction with microfilaments, causing a permanent change of their reticular structure and preventing their depolymerization. The journey towards the determination of the absolute configurtion of reidispongiolide A (and its congeners) commenced with the controlled degradation of the natural macrolide to obtain the three fragments depicted in yellow. The stereoselective synthesis of the fragment highlighted in the square was achieved starting from L ‐malate dimethyl ester shown at the top of the cover. Details are discossed in the article by M. V. D′Auria et al. on page 785 ff.