Sims NJ,
Bonnet WC,
Lawson DM,
Wood JL.
*
Baylor University, Waco, USA
Enantioselective Total Synthesis of (+)-Alterbrassicicene C.
J. Chem. Am. Soc. 2023;
145: 37-40
DOI:
10.1021/jacs.2c12275
Key words
(+)-alterbrassicicene C - ozonolysis - ring-closing metathesis - transannular etherification - Weitz–Scheffer epoxidation - Stille cross-coupling - Meinwald rearrangement
Significance
Wood and co-workers report an asymmetric total synthesis of (+)-alterbrassicicene C, a fusicoccane diterpenoid isolated from the fungal plant pathogen Alternaria brassicicola.
Comment
BCl3-catalyzed diastereoselective opening of tetrahydrofuran J in SN2'-fashion followed by conjugate addition furnishes the unprecedented tetracyclic oxa-bridged ring system of (+)-alterbrassicicene C. BF3-catalyzed Meinwald rearrangement establishes the second enone functionality, after which the natural product could be obtained in two further steps.
