2003
DOI: 10.1021/ol035619v
|View full text |Cite
|
Sign up to set email alerts
|

Total Synthesis of 3‘,5‘-C-Branched Nucleosides

Abstract: [reaction: see text] A novel total synthesis of 3',5'-C-branched uridine azido acid has been accomplished using stereoselective aldehyde alkynylation, Ireland-Claisen rearrangement, and iodolactonization as the key reactions. Compared to traditional routes that start from carbohydrates, the present methodology is more efficient, flexible for future optimization, and provides access to both enantiomers of the products. Because the key chemistry does not involve the 3'- and 5'-C substituents, our route is a gene… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
27
0

Year Published

2005
2005
2020
2020

Publication Types

Select...
3
3

Relationship

1
5

Authors

Journals

citations
Cited by 25 publications
(27 citation statements)
references
References 27 publications
0
27
0
Order By: Relevance
“…This result is an improvement over the route previously developed in our laboratory, which required six steps and gave 29% yield of 2. 4 It should be noted that besides being shorter, easier to scale-up, and more efficient, the new route also provides enantiomerically pure lactones, whereas the previous synthesis yielded products with 92% ee only.…”
mentioning
confidence: 92%
See 4 more Smart Citations
“…This result is an improvement over the route previously developed in our laboratory, which required six steps and gave 29% yield of 2. 4 It should be noted that besides being shorter, easier to scale-up, and more efficient, the new route also provides enantiomerically pure lactones, whereas the previous synthesis yielded products with 92% ee only.…”
mentioning
confidence: 92%
“…3 Asymmetric syntheses that start from small organic molecules are potentially shorter and more efficient routes to highly substituted 2-hydroxy-γ-lactones. [4][5][6] Recently, we reported 4 a total synthesis of 3′,5′-C-branched uridine 1 (Base ) uracyl, TES ) triethylsilyl, TBDPS ) tert-butyldiphenylsilyl, Tr ) trityl) (Scheme 1), which we are using as a monomer for preparation of amide-linked RNA analogues. 7 In our synthesis, we prepared γ-butyrolactone 2 from small achiral molecules (7-9) in only six steps and 29% yield using Ireland-Claisen rearrangement of 5 followed by iodolactonization of 3 as the key steps (Scheme 1).…”
mentioning
confidence: 99%
See 3 more Smart Citations