Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin

The synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product, is described. The synthesis starts with the diketopiperazine nucleus intact and the side chains are installed using iterative aldol condensations. The route represents a general strategy fo...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 15; no. 40; pp. 8634 - 8640
Main Authors Kelley, Elizabeth W., Norman, Skylar G., Scheerer, Jonathan R.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.10.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ISOROQUEFORTINE-C
SPIROTRYPROSTATIN-B
PHENYLAHISTIN DERIVATIVES
(-)-SPIROTRYPROSTATIN B
2,5-DIKETOPIPERAZINES
NATURAL-PRODUCTS
AMINO-ACIDS
STEREOCONTROLLED TOTAL-SYNTHESIS
ROQUEFORTINE-C
3 STEREOISOMERS
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Summary:The synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product, is described. The synthesis starts with the diketopiperazine nucleus intact and the side chains are installed using iterative aldol condensations. The route represents a general strategy for synthesis of a wide array of mono-alkylidene diketopiperazine structures, including those derived from non-canonical amino acid residues.
Bibliography:NIH RePORTER
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02297brsc.li/obc