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Formal total synthesis of platencin.

Georgy N GN Varseev and Martin E ME Maier

Angew Chem Int Ed Engl 48(20):3685-8 (2009) PMID 19353600

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.

DOI: 10.1002/anie.200900447
Version: za2963e q8za9 q8zb2 q8zca q8zd5 q8zea q8zfa q8zgb

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