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Total synthesis and biological evaluation of tyroscherin.

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.

SUBMITTER: Tae HS

PROVIDER: S-EPMC3175621 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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Total synthesis and biological evaluation of tyroscherin.

Tae Hyun Seop HS Hines John J Schneekloth Ashley R AR Crews Craig M CM

Organic letters 20101001 19

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. ...[more]

PMID: 20831175

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