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. 2010 Mar 1;2010(4):667-674.
doi: 10.1055/s-0029-1219376.

Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin

Kai Zhang  1 , Dennis P Curran
Affiliations

Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin

Kai Zhang et al. Synlett. .

Abstract

Four stereoisomers of the C21-C40 fragment are synthesized in a single exercise with the aid of fluorous tagging to encode configurations at C37 and C33. After demixing and detagging, the isomers were found to have substantially identical (1)H NMR spectra. However, there were some small but reliable differences in their (13)C NMR spectra.

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Figures

Figure 1
Figure 1
Proposed structure of tetrafibricin (1)
Scheme 1
Scheme 1
Retrosynthetic analysis of bottom fragment 2
Scheme 2
Scheme 2
Synthesis of sulfone quasiracemate M-3
Scheme 3
Scheme 3
Synthesis of aldehyde quasiracemate M-4
Scheme 4
Scheme 4
Synthesis of single isomer fragment 5
Scheme 5
Scheme 5
Fragment coupling, demixing, and detagging
See this image and copyright information in PMC

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