Stereoselective synthesis of the C1-C5 dienoic sub-unit of bafilomycins via a γ-sulfonyl-δ-lactone intermediate

Synlett

Volumn , Issue 11, 1998, Pages 1223-1226

  Demont, Emmanuel ^a   Lopez, Roman ^a   Férézou, Jean Pierre ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009579321     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1903     Document Type: Article

References (43)

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31. Synthesis of sulfones 3 and 4 will be published elsewhere.
32. In comparative experiments, the reaction of the anion derived from 4-desmethylsulfone analogue of 3 with benzaldehyde or 3-phenylpropionaldehyde led to the expected condensation products in 80-85% yields.
33. This chiral aldehyde was synthesized by ozonolysis of the corresponding Hoppe's homoaldolisation vinylcarbamate adduct prepared for other synthetic work in our laboratories (unpublished results), see Hoppe, D.; Hanko, R.; Brönneke, A.; Lichtenberg, F.; van Hülsen, E. Chem. Ber. 1985, 118, 2822.
34. Hydroxysulfones 6a,b were obtained as 3:1 and 1:1 diastereomeric mixtures respectively whereas the corresponding lactones 7a,b were obtained as 2:1 and 6:5 mixtures. Interestingly, lactone 7c only exists as a ca. 2:1 diastereomeric mixture which probably indicates an efficient diastereoselective Felkin-Ahn controlled condensation.
35. Obtention of δ-lactones after condensation of dianions derived from 4-(phenylsulfonyl)butanoic acid on aldehydes followed by acidic work-up has been precedented whereas the course of the subsequent Na/Hg reductive elimination step has been shown to involve an initial methanolysis of the lactone function, a fact which has not been observed in our examples : Thompson, C. M.; Frick, J. A. J. Org. Chem., 1989, 54, 890.
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41. 2O as above.
42. Calculations including molecular dynamics minimisations via MM2 force fields, MOPAC semi-empirical calculations (MINDO/3) and Monte Carlo research of conformers have been carried out with Macromodel V5.0 (Columbia University) and CS Chemdraw 3D Pro softwares (with H or Me instead of Na when this later was unparametrized).
43. Some of these arguments have been claimed to explain the reactivity of anomeric anions derived from samarium: Mazéas, D.; Skrydstrup, T.; Beau, J. M. Angew. Chem., Int. Ed. Engl 1995, 34, 909.