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Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5--Cycloclavine.

08:00 EDT 14th August 2019 | BioPortfolio

Summary of "Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5--Cycloclavine."

Starting from the commercially available 4-bromoindole, a concise and efficient enantioselective formal synthesis of (+)-cycloclavine () in 13 steps with 2.0% overall yield and a total synthesis of (+)-5--cycloclavine () in 14 steps with 3.3% overall yield were achieved. Key features of the syntheses include the addition of a Grignard reagent to the C═N/Heck reaction sequence to construct the fused 6-5-6 ring systems, cyclopropanation, an ester aminolysis reaction, and the first example of the construction of a 3-azabicyclo[3,1,0]hexane through an intramolecular [3 + 2] cycloaddition/nitrogen extrusion.

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Name: Organic letters
ISSN: 1523-7052
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