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2005
Antibiotics
U 1200
34- 272
Diastereocontrolled Synthesis of Highly Functionalized Spiroketals: Application
to the Synthesis of a Precursor of the C12—C25 Fragment of Bafilomycin A1. —
Spiroketal (I), the precursor of the title fragment of bafilomycin A1 (II), is synthesized
in 20 steps with an overall yield of 6%. The drawbacks concerning the functionalization
at C-16, C-17 and C-18 are partially compensated by the use of only one source of
homochirality (the starting aldehyde). Some of the reaction intermediates or sequences
described such as anti-Danishefsky type intermediate or a cyclopropane-methylation
strategy may be useful for other synthetic applications. — (LOPEZ, R.; POUPON,
J.-C.; PRUNET*, J.; FEREZOU, J.-P.; RICARD, L.; Synthesis 2005, 4, 644-661;
Lab. Synth. Org., CNRS, DCSO, Ec. Polytech., F-91128 Palaiseau, Fr.; Eng.) —
H. Hoennerscheid
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