## Abstract Treatment of thioglycoside (I) with various acceptors under conditions A) allows the stereoselective preparation of the required subunits in good to excellent yields.
A Novel and Highly Stereoselective Synthesis of 2-Substituted Perhydrofuro[2,3- b ]pyran Derivatives
β Scribed by Ma, Xiaofeng; Tian, Qiang; Tang, Qin; Zhao, Jinzhong; Shao, Huawu
- Book ID
- 121191408
- Publisher
- American Chemical Society
- Year
- 2011
- Tongue
- English
- Weight
- 925 KB
- Volume
- 13
- Category
- Article
- ISSN
- 1523-7060
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π SIMILAR VOLUMES
1R,5S)-2,8-Dioxabicyclo[3.3.0]octan-3-one and its derivatives, important subunits in various biologically active natural products, have been synthesized based on a new approach using the asymmetric oxyselenenylation of 2,3-dihydrofuran as the key step.
The reaction of 2-chloromethyl-3-(2-methoxyethoxy)propene with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E 1 ΒΌR 1 R 2 CO) in THF at 278 to 08C, followed by the addition of an epoxide [E 2 ΒΌR 3 R 4 C(O)CHR 5 ] at 0 to 208C leads,