Efficient synthesis of 8-oxa-bicyclo[3.2.1]octane derivatives from d-arabinose
β Scribed by Yi Liu; Tian-Xiang Han; Zhen-Jun Yang; Liang-Ren Zhang; Li-He Zhang
- Book ID
- 108284256
- Publisher
- Elsevier Science
- Year
- 2007
- Tongue
- English
- Weight
- 181 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0957-4166
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The enantioselective deprotonation of the 8-oxabicyclo[3.2. l]octan-3-one with chiral lithium amides 5 and 6, in the presence of LiC1, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral [3-keto esters were reduced with sodium amalgam to afford
## Abstract Alkylation of bicyclo[3.3.0]octaneβ2,8βdione (**1**), which is prepared by a modification of the procedure described in the literature, gives the methylβ and propynylβderivatives **6** and **7** (__Scheme 1__). In addition to the method described previously (__Scheme 2__), 9βmethylβ__ci
New methodology for the synthesis of enantiopure 3-aza-6,8-dioxa-bicyclo[3.2.1]octane-carboxylic acids belonging to 7-endo-BTAa sub-class of g/d amino acids is described. The novelty is the use of 2,3-O-isopropylidene-erythrose instead of meso-tartaric acid derivative, thus allowing us to perform an
Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines. -Asymmetric deprotonation of the racemic ketone (I) using chiral lithium amides provides ready access to the non-racemic Ξ²-ketoesters (III), which can be easily transfor