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New method for the determination of the absolute stereochemistry in antitumoral annonaceous acetogenins

✍ Scribed by M. Carmen González; Catherine Lavaud; Teresa Gallardo; M. Carmen Zafra-Polo; Diego Cortes

Book ID
104208591
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
619 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The al~olute configurations at the carbinol centers in several acetogenins were determined through p-hrem ,oph,~ylmethane derivatives aagl subsequent Mosher ester methodology. This method has been applied on ot,0t'-dihydgoxylated adjacent bis-THF acetogenins with a threa/cis/threa/cis/erythro relative configuration { membiarollin ( 1 ), a new acetogenin isolated from Rollinia membranacea seeds, rollimembrin (2), membxanadn (3) and rulliniastatin-1 (4)}, and a threoltranslthreoltranslerythro relative configm'ation {motrilin (5), square(gin (6), and desacetyluvaxicin (7)}. I was found to be the most potent inhibitor of the mammalian mitochondrial complex I.

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Preparations of 1,2-, 1,3-, 1,5-formaldehyde acetals from the corresponding polyhydroxylated annonaceous acetogenins were performed in good yield. Addition of Et3N to a mixture of DMSO and TMSC1 is crucial to avoid in situ hydrolysis of the intramolecular acetals.