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- Title
Oxidative Coupling Approach to Sarpagine Alkaloids: Total Synthesis of (−)‐Trinervine, Vellosimine, (+)‐Normacusine B, and (−)‐Alstomutinine C.
- Authors
Zhang, Ye; Zhang, Lei; Qi, Xiangbing
- Abstract
Sarpagine alkaloids are bioactive indole natural products that contain a highly rigid indole‐fused 1‐azabicyclo[2.2.2]octane, more than 100 members of which have been identified. Herein, a detailed examination of the intramolecular oxidative coupling between a ketone and a Weinreb amide for assembling the complex 1‐azabicyclo[2.2.2]octane core structure of sarpagine family alkaloids is described. Precise late‐stage manipulations of the ketone and Weinreb amide enable the divergent syntheses of (−)‐trinervine, (+)‐vellosimine, (+)‐normacusine B, and (−)‐alstomutinine C. Other notable transformations of the synthesis featured an aza‐Achmatowicz/indole cyclization cascade to generate the azabicyclo[3.3.1]nonane structure, a regioselective elimination reaction to form the ethylidene motif embedded in the (+)‐vellosimine and (+)‐normacusine B structures, and a diastereoselective indole oxidative rearrangement to form the spirooxindole structure in (−)‐alstomutinine C.
- Subjects
OXIDATIVE coupling; ELIMINATION reactions; KETONES; REGIOSELECTIVITY (Chemistry); FAMILY structure; ALKALOIDS; AZA compounds; ISOQUINOLINE alkaloids
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 28, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202304435