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A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
- Source :
-
Tetrahedron . May2006, Vol. 62 Issue 22, p5223-5247. 25p. - Publication Year :
- 2006
-
Abstract
- Abstract: Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau''amine, are described. A proposed refinement of the Kinnel–Scheuer biosynthetic proposal for palau''amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels–Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau''amine. [Copyright &y& Elsevier]
- Subjects :
- *ORGANIC compounds
*ALKALOIDS
*ORGANONITROGEN compounds
*MICROBIAL metabolites
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 62
- Issue :
- 22
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 20728836
- Full Text :
- https://doi.org/10.1016/j.tet.2005.12.068