Journal
ORGANIC LETTERS
Volume 18, Issue 16, Pages 3952-3955Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01674
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Funding
- NIH (National Institute of General Medical Sciences) [R01GM092870]
- NIH [S10 OD018126]
- National Science Foundation [CHE-1039436, CHE-1126265, CHE-0821501]
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A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring, fragmentation/intramolecular azomethine ylide 1,3-dipolar-cycloaddition reaction sequence the gives the desired tricyclic product as a single diastereomer. A gamma-amino-beta-hydroxy-alpha-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced: to, the corresponding amine.
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