Abstract
Two members of a family of pyrrole-imidazole marine alkaloids, (+)-dibromophakellin and the nonnatural congener (+)-phakellin, were synthesized enantioselectively from 4-hydroxy-L-proline. The chiral aminal at C10 was constructed efficiently by means of an Overman-type [3,3] sigmatropic rearrangement of an enamide (see scheme).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alcohols / chemical synthesis
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Alcohols / chemistry
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Molecular Structure
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Piperazines / chemistry
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Stereoisomerism
Substances
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Alcohols
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Heterocyclic Compounds, 4 or More Rings
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Piperazines
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dibromophakellin
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phakellstatin