✦ LIBER ✦
Functionalized Nitroalkanes in Organic Synthesis. The first concise preparation of 4-hydroxyheptadecan-7-one and 14-hydroxyoctadecan-8-one, two new hydroxy ketones isolated from Chiococca alba
✍ Scribed by Roberto Ballini; Giovanna Bosica; Gianni Rafaiani
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- German
- Weight
- 242 KB
- Volume
- 78
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The 4‐hydroxyheptadecan‐7‐one (1) and 14‐hydroxyoctadecan‐8‐one (2), two new hydroxyketones isolated from leaves of Chiococca alba, were synthesized, for the first time, by hydroxy‐functionalized nitroalkanes 4 and 9, respectively, via two chemoselective key steps: i) nitroaldol condensation with basic alumina, and ii) direct Nef conversion of nitroalkenes to carbonyl derivatives with sodium hypophosphite, in order to preserve the OH group.