Total Synthesis and Biological Evaluation of (−)‐Englerin A and B: Synthesis of Analogues with Improved Activity Profile

A Short Enantioselective Total Synthesis of (−)‐Englerin A

“…2 Furthermore, the oxygen‐bridged bicyclic hydroazulene framework is a challenging molecular structure with seven contiguous stereogenic centers. These two features have triggered intense synthetic work aiming at the preparation of 1 3, 4 and on structure–activity relationship studies 4f. 5 Herein we report an enantioselective total synthesis of (−)‐englerin A ( 1 ) that allows the construction of this bioactive compound in a few preparatively simple steps.…”

Asymmetric Total Synthesis of (−)‐Englerin A through Catalytic Diastereo‐ and Enantioselective Carbonyl Ylide Cycloaddition

“…accomplished the first total synthesis of (+)‐englerin A from (+)‐ trans , cis ‐nepetalactone utilizing an epoxylactone rearrangement, a stereoselective Barbier‐type allylation, a ring‐closing metathesis, and a transannular epoxide opening as the key steps, thereby establishing the previously unknown absolute configuration of natural (−)‐englerin A as shown in 1 5. Since then, eight total syntheses,6 three formal syntheses,7 and several synthetic studies,8 which are all based on innovative strategies and tactics, as well as results of structure‐activity relationship studies5b, 6c, 7c, 9 have been reported.…”

Otto Bayer Award: B. List / Young Scientist Award for Natural Product Research: M. Christmann / BASF Award for Organic Electronics and Einstein Professorship: K. Müllen

“…The Young Scientist Award for Natural Product Research is awarded by DECHEMA (Society for Chemical Engineering and Biotechnology) for outstanding achievements in the field. Mathias Christmann (Technische Universität Dortmund) received the 2012 prize for his contribution to the total synthesis of biologically relevant natural products such the bacterial RNA polymerase inhibitor ripostatin B,2a and englerin A 2b. Christmann studied chemistry at the Technische Universität Braunschweig, and received his PhD in 2001 from the Leibniz Universität Hannover under the direction of Markus Kalesse.…”