Concise syntheses of notoamides B-E and stephacidin A
Date
2008
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Abstract
Presented herein are concise syntheses of the cytotoxic alkaloids notoamides B-E. A highly convergent synthesis is outlined from commercially available 6-hydroxy indole and naturally derived L(-)-Proline or L(-)-cis-3-hydroxy Proline. Also presented is a 16 step synthesis of (±)-11-epi -norgeamide B and finally a concise 17 step synthesis of stephacidin A. The synthesis of each member of the norgeamide and notoamide family of natural products is proposed via the tunable activation or deactivation of the 1,7-dihydropyrano[2,3-g]indole ring system in order to exploit a mild Pinacol-type rearrangement en-route to notoamides A-C and norgeamides A and B, or the prevention thereof, to allow access to the pyrroloindole scaffold of norgeamides C and D or notoamide D.
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Subject
marcfortine
natural products
norgeamide
notoamides
stephacidin
organic chemistry
pharmaceutical sciences