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ChemInform Abstract: Total Synthesis of 15(RS)-5,6-Dehydro-8-epi-PGF2α Methyl Ester by a Biomimetic Process.

✍ Scribed by A. GUY; T. DURAND; J.-P. VIDAL; J.-C. ROSSI

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199724253

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✦ Synopsis

Total Synthesis of 15(RS)-5,6-Dehydro-8-epi-PGF2α Methyl Ester by a Biomimetic Process.

-Using diacetone D-glucose (I) as starting material the first total synthesis of the title compound (IV) is achieved. Key step is a final biomimetic 5-exo-radical cyclization of the highly functionalized precursor (II) using molecular oxygen trapping under classical tin hydride conditions. Compound (IV) is a potential precursor of labelled 8-epi PGF2α by reduction of the triple bond. -(GUY, A.

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