Chemical & Pharmaceutical Bulletin 2013-01-01

Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy.

Machiko Ono, Keisuke Kato, Hiroyuki Akita

文献索引：Chem. Pharm. Bull. 61(4) , 464-70, (2013)

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摘要

Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford γ-lactone or δ-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy-2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5-hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)-parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.

相关化合物

  • 2,4,6-三氯苯酰氯

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