Abstract
Applying a biomimetic approach, the first total synthesis of (±)-tubastrindole B is reported herein. This work features a ring-expansion cascade of a dictazole-type precursor into cycloaplysinopsin-type congeners. Moreover, the isolation of a transient biogenetic intermediate represents a milestone in the biosynthetic understanding of this family of marine alkaloids.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis
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Alkaloids / chemistry
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Animals
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Indoles / chemical synthesis*
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Indoles / chemistry
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Marine Biology
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Molecular Structure
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Porifera / chemistry
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Stereoisomerism
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Tryptophan / analogs & derivatives
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Tryptophan / chemistry
Substances
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Alkaloids
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Indoles
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tubastrindole B
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aplysinopsin
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Tryptophan