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Total synthesis of two novel brominated acetylenic diols (+)-diplyne C and E: stereoselective construction of the (E)-1-bromo-1-alkene |
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| Affiliation: | 1. Department of Physics, College of Education and Linguistics, University of Amran, Yemen;2. Technische Universität Berlin, IOAP, Strasse des 17. Juni 135, Berlin 10623, Germany;3. Helmholtz-Zentrum Berlin, Wilhelm-Conrad-Röntgen-Campus Adlershof, Albert-Einstein-Straße 15, Berlin 12489, Germany;4. DESY, Center for Free Electron Laser Science (CFEL), Notkestr. 85, Hamburg 22607, Germany |
| Abstract: | The total syntheses of the enantiomers of two novel brominated polyacetylenic natural products diplynes C and E are reported. Pd and Cu(I)-catalyzed coupling reactions were employed to synthesize the diyne and enyne units. The stereochemistry of the terminal (E)-alkenyl bromide in diplyne C was constructed stereoselectively using Brown’s hydroboration–bromination procedure. The stereochemistry of the internal (E)-double bond in diplyne E was established using a Takai reaction. The stereocenter was derived from d-mannitol. |
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