A New Modular Indole Synthesis. Construction of the Highly Strained CDEF Parent Tetracycle of Nodulisporic Acids A and B

A New Modular Indole Synthesis. Construction of the Highly Strained CDEF Parent Tetracycle of Nodulisporic Acids A and B

Construction of the highly strained CDEF parent tetracycle, a structural motif found only in the potent ectoparasiticidal agents (+)-nodulisporic acids A and B and related congeners, has been achieved via a new modular indole synthesis, exploiting a sequential Stille cross-coupling/Buchwald−Hartwig...

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Veröffentlicht in:Organic letters 2006-05, Vol.8 (10), p.2167-2170
Hauptverfasser: Smith, Amos B, Kürti, László, Davulcu, Akin H
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:Construction of the highly strained CDEF parent tetracycle, a structural motif found only in the potent ectoparasiticidal agents (+)-nodulisporic acids A and B and related congeners, has been achieved via a new modular indole synthesis, exploiting a sequential Stille cross-coupling/Buchwald−Hartwig union/cyclization tactic. The new indole synthesis holds the promise of rapid assembly of diverse, highly substituted indoles possessing uncommon substitution patterns.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0606536