Construction of the Zaragozic Acids Core Bicycle

Masayoshi Tsubuki; Hiroyuki Okita; Toshio Honda

doi:10.1055/s-1998-1988

Synlett 1998; 1998(12): 1417-1419
DOI: 10.1055/s-1998-1988

letter

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Construction of the Zaragozic Acids Core Bicycle

Masayoshi Tsubuki^* , Hiroyuki Okita, Toshio Honda

^*Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan; Fax 81-3-5498-5791; E-mail: honda@hoshi.ac.jp

Abstract

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Concise synthesis of the bicyclic core of zaragozic acids has been accomplished by the utilization of (2S,3S)-furylglycerol 7. The key features are based on the diastereoselective dihydroxylation of enone 8 followed by reduction of ketone 11 to control the stereochemistries at the C4-C6 positions of the target molecule. Addition of lithium trimethylsilylacetylide to aldehyde 20 provided propargyl alcohol 21, which was further transformed into the bicyclic core 25, a potent intermediate for the synthesis of zaragozic acids.

synthesis - zaragozic acid - squalestatin - furylglycerol 2,8-dioxabicyclo[3.2.1]octane

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