What type of study is this?

This is a Total Synthesis study.

September 10, 2025

Total Synthesis of (±)-Crokonoid A

Key Points

The successful total synthesis of (±)-crokonoid A showcases a unique carbon structure and oxidation pattern.
Key features include effective construction of a tricyclo scaffold through regio- and diastereoselective reactions.
A novel approach involving nitrile-oxide dipolar cycloaddition facilitated the synthesis of the bicyclo framework.
This work contributes to the chemistry of ent-kauranoids, paving the way for further explorations of complex synthetic strategies.

Abstract

We report the first total synthesis of (±)-crokonoid A, a highly oxidized and rearranged ent-kauranoid featuring a novel tricyclo4.4.1.11,4dodecane scaffold. The unique double bridged carbon skeleton was assembled by synthesis of the bicyclo4.3.1decane via nitrile-oxide dipolar cycloaddition. Salient features of this strategy are the effective construction of the bridged system and masking the twofold aldol motif as an isoxazoline. An unconventional bridgehead propargylation set the key quaternary stereocenter concomitant with the installation of the side chain. Subsequent cycloalkenylation led to construction of the bicyclo3.2.1octane, completing the carboskeleton. Strategic orchestration involving regio- and diastereoselective reactions furnished the unique oxidation pattern, thus completing the total synthesis.

Bookmark

Cite This Study

Martini et al. (Fri,) studied this question.

synapsesocial.com/papers/68c1c64554b1d3bfb60f29c0 https://doi.org/https://doi.org/10.1021/jacs.5c11026

Bookmark