Issue 61, 2024

Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one

Abstract

Enantioselective total synthesis of (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one has been accomplished starting from enantiopure Wieland–Miescher ketone. Key features of the syntheses include a benzannulation step to construct the tricyclic core, an oxidative dearomatization step to generate the diene, and a Diels–Alder reaction with ethylene gas to establish the bicyclo[2.2.2]octane framework. Efficient late-stage functionalisation of the A-ring by aerobic oxidation and Baeyer−Villiger oxidation completed the atisane target molecules.

Graphical abstract: Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
25 Apr 2024
Accepted
03 Jun 2024
First published
03 Jun 2024

Chem. Commun., 2024,60, 7866-7869

Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one

D. H. Dethe, N. Sharma, S. Juyal, P. Singh and S. A. Siddiqui, Chem. Commun., 2024, 60, 7866 DOI: 10.1039/D4CC01982B

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