Method for the efficient synthesis of highly-substituted oxetan- and azetidin-, dihydrofuran- and pyrrolidin-3-ones and its application to the synthesis of (±)-pseudodeflectusin.

Tomohiro Maegawa, Kazuki Otake, Keiichi Hirosawa, Akihiro Goto, Hiromichi Fujioka

Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.

Organic letters 2012 Sep 21

filter terms:

Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (±)-pseudodeflectusin based on the new methodology was achieved.

Citation

Tomohiro Maegawa, Kazuki Otake, Keiichi Hirosawa, Akihiro Goto, Hiromichi Fujioka. Method for the efficient synthesis of highly-substituted oxetan- and azetidin-, dihydrofuran- and pyrrolidin-3-ones and its application to the synthesis of (±)-pseudodeflectusin. Organic letters. 2012 Sep 21;14(18):4798-801