Journal of the American Chemical Society p. 4368 - 4378 (1988)
Update date:2022-08-03
Topics: Column chromatography Catalyst Mass spectrometry Nucleophile Stereochemistry Total synthesis Reagent Protecting group Nuclear Magnetic Resonance (NMR) Chemical Synthesis
Danishefsky
Selnick
Zelle
DeNimo
The total synthesis of the title compound, which is a zinc-binding antibiotic, is described. The synthesis starts with aldehyde 4 and Grignard reagent 6. The key steps are (i) the cyclocondensation of aldehyde 10 with diene 11 under the influence of magnesium bromide, (ii) the cyclocondensation of aldehyde 24 with diene 33 under the influence of BF3·OEt2, (iii) the carbon Ferrier reaction of glycal acetate 37 with (E)-crotyltrimethylsilane, and (iv) the reductive merger of aldehyde 2a with sulfone 3.
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