Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin‑, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin

• Published in: Organic letters Vol. 14; no. 18; pp. 4798 - 4801
• Main Authors: Maegawa, Tomohiro, Otake, Kazuki, Hirosawa, Keiichi, Goto, Akihiro, Fujioka, Hiromichi
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.09.2012; Amer Chemical Soc
• Subjects: Alkenes - chemical synthesis; Alkenes - chemistry; Azetidines - chemical synthesis; Azetidines - chemistry; Catalysis; Chemistry; Chemistry, Organic; Chromans - chemical synthesis; Chromans - chemistry; Combinatorial Chemistry Techniques; Cyclization; Furans - chemical synthesis; Furans - chemistry; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Molecular Structure; Physical Sciences; Pyrrolidinones - chemical synthesis; Pyrrolidinones - chemistry; Science & Technology; Stereoisomerism; OXETAN-3-ONES; REACTIVITY; DRUG DISCOVERY; ALPHA-ALKOXYPHOSPHONIUM SALTS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol302096j

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.