Synthesis of methyl-substituted trans-fused tetrahydropyrans via 6-endo cyclization
โ Scribed by Yuji Mori; Hiroki Furuta; Toyohisa Takase; Shinjiro Mitsuoka; Hiroshi Furukawa
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 241 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A stereocontrolled synthesis of methyl-substituted trans-fused tetrahydropyrans having methyl groups adjacent to the ring oxygen is described. The strategy involves the coupling reaction of sulfonyl-stabilized oxiranyl anions with triflates and 6-endo cyclization of their products.
๐ SIMILAR VOLUMES
Acid-catalyzed cyclization of hydroxy-cyclic sulfates occurs with endo-regioselectivity affording bispyran products from substrates in which the nucleophilic hydroxyl and electrophilic cyclic sulfate groups are 1,2-trans-substituted on a cyclic pyran template. This methodology is demonstrated in an
Synthesis of trans-syn-trans Fused Bis-Pyrans via endo-Selective Cyclizations of Cyclic Sulfates. -The first examples of pyran ring formation from hydroxy-cyclic sulfate cyclization are reported. Thus, acid-catalyzed endo-regioselective cyclization of compounds (II) afford the trans-syn-trans fused