89030-27-3Relevant academic research and scientific papers
An Useful Synthetic Method for 3-Substituted δ-Lactones. Synthesis of (+/-)-Secocrispiolide
Kato, Michiharu,Ouchi, Akihiko,Yoshikoshi, Akira
, p. 1479 - 1486 (2007/10/02)
2-Phenylthio-2-penten-5-olide (1) acted as a reactive Michael acceptor toward some typical carbon nucleophiles to give 3-substituted 2-phenylthio-5-pentanolides (2) which were convertible both to 3-substituted 5-pentanolides by reductive desulfurization and to 3-substituted 2-penten-5-olides by sulfenic acid syn elimination of the sulfoxides 4 derived from 2.The Pummerer rearrangement of 4 provided 3-substituted 2-phenylthio-2-penten-5-olides and/or 2-hydroxy-2-penten-5-olides. (+/-)-Secocrispiolide was synthesized via the adduct obtained by the Michael reaction of 1 with the Grignard reagent prepared from 2,6-dimethylbenzyl bromide and magnesium.
2-(PHENYLTHIO)-2-PENTEN-5-OLIDE, A NEW BUILDING BLOCK FOR THE SYNTHESIS OF 3-SUBSTITUTED γ-LACTONES
Kato, Michiharu,Ouchi, Akihiko,Yoshikoshi, Akira
, p. 1511 - 1514 (2007/10/02)
2-(Phenylthio)-2-penten-5-olide, readily accessible from γ-valerolactone, showed high electrophilic reactivities toward some typical carbon nucleophiles to give 3-substituted 2-(phenylthio)pentanolides, which were convertible to a variety of 3-substituted
