A stereoselective approach for the synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin from L-ascorbic acid has been described. The key steps are highly stereoselective nucleophilic addition reaction on aldehyde 8 and also a single pot transformation of 15 to (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brev
Stereoselective Synthesis of (−)-(1 R ,1′ R ,5′ R ,7′ R )-1-Hydroxy- exo -brevicomin and (+)- exo -Brevicomin from 3,4,6-Tri- O -acetyl- D -glucal
✍ Scribed by Sabitha, Gowravaram; Maheswara Reddy, Arekuti; Siva Sankara Reddy, Singam; Singh Yadav, Jhillu
- Book ID
- 120833693
- Publisher
- John Wiley and Sons
- Year
- 2013
- Tongue
- German
- Weight
- 182 KB
- Volume
- 96
- Category
- Article
- ISSN
- 0018-019X
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## Abstract Both (1__R__)‐ and (1__S__)‐hydroxy derivatives of (+)‐exo‐brevicomin {(1__R__,1′__R__,5′__R__,7′__R__)‐1‐(5′‐methyl‐6′,8′‐dioxabicyclo[3.2.1]‐octyl)ethanol (1) and its (1__S__)‐isomer (2)} were synthesized by employing Sharpless asymmetric dihydroxylation as the key reaction.
## Abstract Both (2__R__)‐ and (2__S__)‐hydroxy derivatives of (+)‐exo‐brevicomin {5‐methyl‐6,8‐dioxabicyclo[3.2.1]octan‐2‐ol; 1 and 2} were synthesized by employing Sharpless asymmetric dihydroxylation as the key reaction.