TY  - JOUR
U1  - Zeitschriftenartikel, wissenschaftlich - begutachtet (reviewed)
A1  - Movahhed, Sohajl
A1  - Westphal, Julia
A1  - Kempa, Alexander
A1  - Schumacher, Christian Eric
A1  - Sperlich, Julia
A1  - Neudörfl, Jörg‐Martin
A1  - Teusch, Nicole
A1  - Hochgürtel, Matthias
A1  - Schmalz, Hans‐Günther
T1  - Total Synthesis of (+)‐Erogorgiaene and the Pseudopterosin A−F Aglycone via Enantioselective Cobalt‐Catalyzed Hydrovinylation
JF  - Chemistry – A European Journal
N2  - Abstract
Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt‐catalyzed hydrovinylation as the chirogenic step. Other noteworthy C−C bond forming transformations include diastereoselective Lewis acid‐mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4‐methyl‐styrene the anti‐tubercular agent (+)‐erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti‐inflammatory activity (inhibition of LPS‐induced NF‐κB activation) as a natural mixture of pseudopterosins A−D or iso‐pseudopterosin A, prepared by β‐D‐xylosylation of the synthetic aglycone.
KW  - Diterpene
KW  - Cationic Cyclization
KW  - Cobalt Catalysis
KW  - Diterpenes
KW  - Glycosides
KW  - Hydrovinylation
KW  - Marine Natural Products
KW  - Glykoside
Y1  - 2021
UN  - https://nbn-resolving.org/urn:nbn:de:hbz:832-epub4-19557
U6  - https://doi.org/10.1002/chem.202101863
DO  - https://doi.org/10.1002/chem.202101863
VL  - 27
IS  - 45
SP  - 11574
EP  - 11579
S1  - 6
ER  -