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ChemInform Abstract: Chemoenzymatic and Ring E-Modular Approach to the (-)-Podophyllotoxin Skeleton. Synthesis of 3′,4′,5′-Tridemethoxy-(-)-podophyllotoxin.

✍ Scribed by D. B. BERKOWITZ; J.-H. MAENG; A. H. DANTZIG; R. L. SHEPARD; B. H. NORMAN

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Chemoenzymatic and Ring E-Modular Approach to the (-)-Podophyllotoxin Skeleton.

Synthesis of 3',4',5'-Tridemethoxy-(-)-podophyllotoxin.

-The first ring E deoxygenated derivative (XI) of the antimitotic (-)-podophyllotoxin (XII) is synthesized. The key steps are the introduction of the absolute stereochemistry by enzyme catalyzed hydrolysis of the diester (II) and the Cu(I) mediated arylation of the Michael acceptor (IV) at a late stage of this synthesis. The last three steps are influenced by the different behaviour of the cis-lactone (VII) and its epimerized trans-isomer (VIII) during the Sem deprotection using modified Kim conditions. -(BERKOWITZ, D.

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