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Synthesis of carbon-14 and tritium labeled analogs of Manoalide

✍ Scribed by S. G. Senderoff; A. Y. L. Shu; K. Lawrie; J. R. Heys

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
833 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Several Manoalide analogs, 4‐(1‐acetyloxyalkyl)‐5‐hydroxy‐2(5H)‐furanones labeled with carbon‐14 in the alkyl side chain, were synthesized. The key step in these syntheses was singlet oxygenation of 2‐trialkylsilyl‐4‐alkylfurans to give the corresponding 4‐alkyl‐5‐hydroxy‐2(5H)‐furanones. The carbon‐14 label in the side chain was introduced earlier in the synthesis by reaction of the desired labeled alkyl Grignard reagent with the appropriate 2‐trialkylsilyl‐4‐furancarboxaldehyde and trapping of the resulting magnesium alkoxide with acetic anhydride. Labeled n‐alkyl Grignard reagents were obtained by carbonation of the corresponding nor‐alkyl bromides using ultrapure magnesium metal and barium carbonate‐ ^14^C followed by reduction of the resulting acid to the alcohol. Bromination followed by metallation gave the desired reagents. Manoalide analogs bearing a carbon‐14 or tritium label in the acetyl moiety of the side chain were synthesized by acetylation of the desired sidechain alcohol with acetyl chloride‐1‐ ^14^C, and by acetylation of the desired alcohol with dibromoacetic acid‐DCC followed by catalytic halogen‐tritium exchange and completion of the synthesis.

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