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Synfacts 2023; 19(03): 0213
DOI: 10.1055/s-0042-1753349
Synthesis of Natural Products

Synthesis of (+)-Alterbrassicicene C

Contributor(s):
Erick M. Carreira
,
Henrik R. Wilke
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
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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.


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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.


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Publication History

Article published online:
13 February 2023

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