4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids
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Details
| Original language | English |
|---|---|
| Pages (from-to) | 836-840 |
| Number of pages | 5 |
| Journal | Zeitschrift fur Naturforschung Section B: A Journal of Chemical Sciences |
| Volume | 68 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Jul 2013 |
| Publication type | A1 Journal article-refereed |
Abstract
A new approach to gamma-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the alpha-hydroxy group by benzylation and subsequent deprotection of the beta-hydroxy group.
Keywords
- Butenolides, Cyclizations, O-Heterocycles, Oxalic Acid, Silyl Enol Ethers, CROSS-COUPLING REACTIONS, STEREOSELECTIVE-SYNTHESIS, EFFICIENT SYNTHESIS, ASCORBIC-ACID, ALKYLIDENEBUTENOLIDES, CYCLIZATION, CHEMISTRY, ETHERS