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A symmetry-based approach to zaragozic acid: Synthesis and end-differentiation of an advanced intermediate

✍ Scribed by Kevin D. Freeman-Cook; Randall L. Halcomb

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 278 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01959-5

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✦ Synopsis

Reported is a novel, symmetry-based strategy for the synthesis of the zaragozic acids. Two enantioselective dihyroxylations are used to set the absolute stereochemistry of a C-2 symmetric intermediate. A sequence of a furan photo-oxidation followed by a diastereoselective dihydroxylation breaks the symmetry and sets two quaternary stereocenters. Finally, a group selective lactonization is used to protect one of two secondary hydroxyls. This accomplishes the critical end-differentiation of this intermediate. An approach to protecting group removal and oxidation is also presented.

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