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Org Lett. 2010 Oct 1;12(19):4308-11. doi: 10.1021/ol101801u.

Total synthesis and biological evaluation of tyroscherin.

Author information

1
Department of Molecular, Cellular, and Developmental Biology, Yale University, New Haven, Connecticut 06511, USA.

Abstract

The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry, facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.

PMID:
20831175
PMCID:
PMC3175621
DOI:
10.1021/ol101801u
[Indexed for MEDLINE]
Free PMC Article

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