Dihyro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide
✍ Scribed by Cere, Vanda; Mazzini, Claudio; Paolucci, Claudio; Pollicino, Salvatore; Fava, Antonino
- Book ID
- 115534688
- Publisher
- American Chemical Society
- Year
- 1993
- Tongue
- English
- Weight
- 760 KB
- Volume
- 58
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
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
## 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.