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Magnesiate Addition/Ring-Expansion Strategy To Access the 6-7-6 Tricyclic Core of Hetisine-Type C20-Diterpenoid Alkaloids.
- Source :
-
Organic Letters . Sep2017, Vol. 19 Issue 17, p4632-4635. 4p. - Publication Year :
- 2017
-
Abstract
- A synthetic strategy to access the fused 6-7-6 tricyclic core of hetisine-type C20-diterpenoid alkaloids is reported. This strategy employs a Diels-Alder cycloaddition to assemble a fused bicyclic anhydride intermediate, which is elaborated to a vinyl lactone-acetal bearing an aromatic ring in five steps. Aromatic iodination is followed by magnesium-halogen exchange with a trialkyl magnesiate species, which undergoes intramolecular cyclization. Subsequent oxidation provides the desired 6-7-6 tricyclic diketoaldehyde, with carbonyl groups at all three positions for eventual C-N bond formation and subsequent elaboration. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 19
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 124966674
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b02260