A concise enantiocontrolled route to yohimbones using a bicyclo[3.2.1]octane chiral building block
โ Scribed by Norio Miyazawa; Kunio Ogasawara
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 91 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
Starting from a common man-made chiral sugar building block, five out of eight L-aldohexoses have been synthesized in a diastereocontrolled manner to complete an integrated synthesis of the eight possible aldohexoses; the remaining three L-hexoses were synthesized from the same building block. Thus,
The intramolecular ene reaction of the 1,6-diene on a bicyclo[3.2.1]octane framework proceeds in a highly diastereoselective manner to form a trisubstituted pyrrolidine on the pyran ring in excellent yield. Its stereochemistry has been determined unambiguously by converting it into the known compoun