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Formal Total Synthesis of Platencin

✍ Scribed by Georgy N. Varseev; Martin E. Maier

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
349 KB
Volume
48
Category
Article
ISSN
0044-8249

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✦ Synopsis

Abstract

The right bicycle: A concise formal synthesis of platencin was based on an efficient oxygen‐mediated palladium‐catalyzed cycloalkenylation of 1 to form a bicyclo[3.2.1]octane, and a deoxygenative rearrangement of tosylhydrazone 2 to construct the bicyclo[2.2.2]octane 3. The total yield of the core structure 4 of platencin was 17.5 % for 13 steps from a commercially available compound. Ts=p‐toluenesulfonyl, TBS=tert‐butyldimethylsilyl, Piv=pivaloyl.magnified image

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