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Communication | Special issue | Vol 40, No. 1, 1995, pp.93-96
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S15
A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-SN2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives

Johann Mulzer* and Stefan Greifenberg

*Institut fur Organische Chemie, Freien Universitat Berlin, Takustrasse 3 D-14195 Berlin, Germany


A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and SN2’-cyclization reactions (9b10a/b via 11a/b).