Total Synthesis of Gombamide A

The first total synthesis of Gombamide A (1), a cytotoxic cyclic thiopeptide from the sponge Clathria gombawuiensis, has been achieved. Highlights of the convergent synthesis feature a disulfide bond forming cascade to close the 17-membered macrocycle and a selenoazidylation procedure to access the...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 15; pp. 3810 - 3813
Main Authors Garcia-Barrantes, Pedro M, Lindsley, Craig W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.08.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHARMACOLOGICAL PROPERTIES
METABOLITES
BE-22179
THIOCORALINE
GLYCALS
DERIVATIVES
PEPTIDE
ALKALOIDS
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Summary:The first total synthesis of Gombamide A (1), a cytotoxic cyclic thiopeptide from the sponge Clathria gombawuiensis, has been achieved. Highlights of the convergent synthesis feature a disulfide bond forming cascade to close the 17-membered macrocycle and a selenoazidylation procedure to access the unusual para-hydroxystyrlyamide (pHSA) moiety. The synthesis required 18 steps, 11 steps in its longest linear sequence, and proceeded in 9.1% overall yield. This work will facilitate the study of the biological effects of Gombamide A and provide groundwork to explore the structure–activity relationship around this rare natural product.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01825