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Paper | Special issue | Vol 67, No. 2, 2006, pp.731-748
Published online, 16th September, 2005
DOI: 10.3987/COM-05-S(T)71
Synthesis of Dioxabicyclo[3.2.1]octane Core of the Zaragozic Acids

Masayoshi Tsubuki,* Hiroyuki Okita, and Toshio Honda*

*Institute of Medical Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Synthesis of the bicyclic core of zaragozic acids employing chiral furylglycerol (6) is described. Key steps are stereoselective construction of the C4 to C6 carbon centers by syn-dihydroxylation of alkene followed by reduction of carbonyl group in pyranone (8), introduction of ethynyl moiety as a carboxylic acid synthon at C3 by nucleophilic addition of lithium trimethylsilylacetylide to aldehyde (19), and bicyclic formation of dihydroxy ketone by ketalization, providing the 2,8-dioxabicyclo[3.2.1]octane core of zaragozic acids.