Bulletin of the Chemical Society of Japan p. 3599 - 3609 (1995)
Update date:2022-08-02
Topics:
Kayano
Yajima
Akazome
Fujita
Ogura
A novel synthetic route to highly substituted γ-lactones was achieved by an intermolecular radical addition to 4-(methylthio)-4-(p-tolylsulfonyl)-3-butenoic ester (1) and its 2-(ethoxycarbonyl) derivative (2), which were easily prepared from (methylthio)methyl p-tolyl sulfone. Upon the irradiation of a solution of 1 and benzophenone in an alcohol (R1R2CHOH), the 1-hydroxyalkyl radical (R1R2C-OH) was generated and added regiospecifically to the 3-position of 1 to form an adduct that led to a γ-lactone by spontaneous intramolecular condensation. Similarly, 2 reacted with the alcohol to give α-(ethoxycarbonyl)-γ-lactones. The alcohol, which is a high boiling liquid or solid, can be employed in the form of a solution (10 molar amounts in acetonitrile) without greatly lowering the reaction efficiency.
View MoreJiangsu Zhenfang Chemical CO.,LTD.(Suzhou Zhenfang Chemical Factory)
Contact:+86-512-69598882
Address:Room1201, Jiayuan Road No.1018, Xiangcheng District, Suzhou, China
ShangHai Ruiyi Medical Technology Co.,Ltd.
Contact:+86-21-54718086
Address:No951 Jianchuan RD,Minhang District
Contact:27-792-602929
Address:SIDNEY MUFAMADI STREET 009949 X44 0700 POLOKWANE,LIMPOPO
Shanghai Coupling Pharmaceutical R&D Co., Ltd.
Contact:+86 021 50106671
Address:403 Room No.4 Buiding, No. 526 Ruiqing Road, Shanghai Zhangjiang Hi-Tech Park
Contact:+86-519-86339586,13584329896
Address:Changzhou Scientific and Education Park
Doi:10.1021/jo070762d
(2007)Doi:10.1039/c39840001073
(1984)Doi:10.1021/ja065601q
(2006)Doi:10.1021/jo0709450
(2007)Doi:10.1021/jm50001a005
(1985)Doi:10.1021/jm00033a017
(1994)