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Synfacts 2010(11): 1215-1215
DOI: 10.1055/s-0030-1258712
DOI: 10.1055/s-0030-1258712
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Microcin SF608
Contributor(s):Steven V. Ley, Philippa B. CranwellS. Diethelm, C. S. Schindler, E. M. Carreira*
ETH Zürich, Switzerland
Synthesis of Microcin SF608 through Nucleophilic Opening of an Oxabicyclo[2.2.1]heptane
Org. Lett. 2010, 12: 3950-3953
ETH Zürich, Switzerland
Synthesis of Microcin SF608 through Nucleophilic Opening of an Oxabicyclo[2.2.1]heptane
Org. Lett. 2010, 12: 3950-3953
Further Information
Publication History
Publication Date:
21 October 2010 (online)
Key words
regioselective epoxide reduction - ring opening - carboxy hydroxyoctahydroindole core
Significance
Microcin SF608, a member of the aeruginosin family, is a serine protease inhibitor isolated in 1999. It displays selective activity against serine protease trypsin over chymotrypsin.
Comment
The TMSOTf-mediated opening of oxabicycle H furnished the octahydroindole core, which was deprotected and coupled to acid I to furnish bicycle J. Removal of the superfluous hydroxyl groups at C3a and C5 was achieved by functionalization of the alcohol as a 3-CF3-substituted benzoate followed by UV irradiation.