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Chemical, enzymatic and microbiological synthesis of 8,12-eudesmanolides: Synthesis of sivasinolide and yomogin analogues

✍ Scribed by Andrés García-Granados; Andrés Parra; Yolanda Simeó; Antonio L. Extremera

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
779 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Conversion of cx-santonin into 8,12-eudesmanolides was accomplished by chemical, enzymatic and microbiological means. Catalytic hydrogenation of ~-santonin gave a mixture of hexahydro derivatives, which were sequentially isolated by lipase-catalysed selective acylation. Reduction of the 6ct-lactone ring, chemical acetylation and enzymatic selective deacetylation gave an eudesmane with a hydroxymethylene group al C-12. which was hydroxylated at C-8 by Rhizopus ntgricans. Finally lactonization with TPAP allowed us to obtain 8.12-eudesmanolides.

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