Asymmetric Total Syntheses and Structure Confirmation of Chlorofucins and Bromofucins.
| Autor: | Kim B; College of Pharmacy, Seoul National University, Seoul, 151-742, Korea., Sohn TI; College of Pharmacy, Seoul National University, Seoul, 151-742, Korea., Kim D; College of Pharmacy, Seoul National University, Seoul, 151-742, Korea., Paton RS; Department of Chemistry, Colorado State University, Fort Collins, 80523, USA. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 Feb 21; Vol. 24 (11), pp. 2634-2642. Date of Electronic Publication: 2018 Jan 25. |
| DOI: | 10.1002/chem.201704564 |
| Abstrakt: | Substrate-controlled asymmetric total syntheses and structure confirmation of (+)-(3E)- and (-)-(3Z)-chlorofucin [(E)-1 a and (Z)-1 a], and (+)-(3E)- and (-)-(3Z)-bromofucin [(E)-1 b and (Z)-1 b] were accomplished. Our syntheses feature as key steps haloetherification (either 'conventional' or 'one-pot organoselenium-mediated') of α,α'-trans-γ,δ-unsaturated oxocene alcohol 9 and our (E)- and (Z)-selective cross-metathesis (CM) protocols. More importantly, a rationale is provided for the strikingly different pathways followed by α,α'-trans-γ,δ-unsaturated oxocene alcohol 9 and its α,α'-cis isomer 9' in the presence of different electrophiles during the intramolecular electrophilic addition reactions. (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.) |
| Databáze: | MEDLINE |
| Externí odkaz: |
|