131771-61-4Relevant articles and documents
Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy
Ono, Machiko,Kato, Keisuke,Akita, Hiroyuki
, p. 464 - 470 (2013/06/05)
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 ?-lactone or d-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.
A Convenient Synthesis of Pyranoid Ene Lactones from Phenyl Glycosyl Sulfones
Qiu, Dongxu,Schmidt, Richard R.
, p. 875 - 877 (2007/10/02)
O-Benzyl protected pyranoid ene lactones (5,6-dihydro-2H-pyran-2-ones) 4a-c, 8 were obtained in high yield in a two-step procedure.Treatment of the phenyl glycosyl sulfones 2a-d, 6, which were readily prepared from their corresponding sulfides, with lithi