Studies on the biosynthesis of the stephacidins andnotoamides. Total synthesis of notoamide S

Timothy J. McAfoos; Shengying Li; Sachiko Tsukamoto; David H. Sherman; Robert M. Williams

doi:10.3987/COM-10-S(E)19

Studies on the biosynthesis of the stephacidins andnotoamides. Total synthesis of notoamide S

Timothy J. McAfoos, Shengying Li, Sachiko Tsukamoto, David H. Sherman, Robert M. Williams

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Notoamide S has been suggested to be the final common precursor between two different Aspergillus sp. fungal strains before diverging to form enantiomerically opposite natural products (+)- and (-)-stephacidin A and (+)-and (-)-notoamide B. The synthesis of notoamide S comes from the coupling of N-Fmoc proline with a 6-hydroxy-7-prenyl-2-reverse prenyl tryptophan derivative that was synthesized via a late stage Claisen rearrangement from a 6-propargyl-2-reverse prenylated indole.

Original language	English (US)
Pages (from-to)	461-472
Number of pages	12
Journal	Heterocycles
Volume	82
Issue number	1
DOIs	https://doi.org/10.3987/COM-10-S(E)19
State	Published - 2010
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Notoamide S has been suggested to be the final common precursor between two different Aspergillus sp. fungal strains before diverging to form enantiomerically opposite natural products (+)- and (-)-stephacidin A and (+)-and (-)-notoamide B. The synthesis of notoamide S comes from the coupling of N-Fmoc proline with a 6-hydroxy-7-prenyl-2-reverse prenyl tryptophan derivative that was synthesized via a late stage Claisen rearrangement from a 6-propargyl-2-reverse prenylated indole.",

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AU - Li, Shengying

AU - Tsukamoto, Sachiko

AU - Sherman, David H.

AU - Williams, Robert M.

PY - 2010

Y1 - 2010

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AB - Notoamide S has been suggested to be the final common precursor between two different Aspergillus sp. fungal strains before diverging to form enantiomerically opposite natural products (+)- and (-)-stephacidin A and (+)-and (-)-notoamide B. The synthesis of notoamide S comes from the coupling of N-Fmoc proline with a 6-hydroxy-7-prenyl-2-reverse prenyl tryptophan derivative that was synthesized via a late stage Claisen rearrangement from a 6-propargyl-2-reverse prenylated indole.

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Studies on the biosynthesis of the stephacidins andnotoamides. Total synthesis of notoamide S

Abstract

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