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- Title
Synthesis of O,S-Containing Polycycles via One-Pot Michael Addition-Cycloacetalisation Cascade.
- Authors
Bankar, Siddheshwar K.; Shirke, Rajendra P.; Ramasastry, S. S. V.
- Abstract
An efficient diversity-oriented approach for the synthesis of previously unknown di-, tri-, tetra- and spirocyclic pyrano-1,4-dioxinones, pyrano-1,4-dithiinones and pyrano-1,4-oxathiinones from readily available starting compounds has been described. Cascade Michael addition-cycloacetalisation of acetoxy-, alkoxy-, and aryloxypyranones and 1,2-dinucleophiles under mild Lewis acidic conditions provides a direct access to oxygen and sulfur-containing complex heterocycles. Mechanistic aspects of the cascade process were elucidated in light of experimental facts. The methodology described herein shows high promise for the synthesis of several bioactive natural products as well as pharmaceutically important compounds.
- Subjects
HETEROCYCLIC compounds synthesis; MICHAEL reaction; LEWIS acids; PYRANONES synthesis; NATURAL products
- Publication
Advanced Synthesis & Catalysis, 2015, Vol 357, Issue 14/15, p3284
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201500505