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Synthesis of (E)‐4‐Bromo‐3‐methoxybut‐3‐en‐2‐one,the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A–C |
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| Authors: | Alejandro Gil Dr. Janire Lamariano‐Merketegi Dr. Adriana Lorente Prof. Fernando Albericio Prof. Mercedes Álvarez |
| Affiliation: | 1. Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona, Barcelona, Spain;2. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona, Spain;3. University of Zurich, Zürich, Switzerland;4. Department of Organic Chemistry, University of Barcelona, Barcelona, Spain;5. School of Chemistry, University of Kwa-Zulu-Natal, Durban, South Africa;6. Laboratory of Organic Chemistry, Faculty of Pharmacy, Barcelona, Spain |
| Abstract: | The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4‐bromo‐3‐methoxybut‐3‐en‐2‐ones are described. Furthermore, a preliminary study to successfully introduce the BMD within the polyol chain and the fatty acid allowed us to corroborate the end structure of the polyol. |
| Keywords: | enantioselectivity Mukaiyama aldol addition natural products synthesis Wittig olefination |