129444-74-2

Upstream product

• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 212185-22-3 (5R,6R)-6-(3,3-diethoxypropyl)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one 
• 1382088-10-9 C₂₇H₂₇F₅O₄S 
• 97640-44-3 isospongia-13,15-dien-20-oic acid 
• 225653-32-7 4-[(1S,4R,5R)-4-(3,3-Diethoxy-propyl)-5-isopropenyl-2,4-dimethyl-3-vinyl-cyclohex-2-enyloxy]-but-2-ynoic acid methyl ester 
• 225653-31-6 (3R,4R,6S)-3-(3,3-Diethoxy-propyl)-4-isopropenyl-1,3-dimethyl-6-prop-2-ynyloxy-2-vinyl-cyclohexene 
• 225653-30-5 (1S,4R,5R)-4-(3,3-Diethoxy-propyl)-5-isopropenyl-2,4-dimethyl-3-vinyl-cyclohex-2-enol 
• 225653-29-2 (3S,5R,6R)-6-(3,3-Diethoxy-propyl)-3-hydroxy-5-isopropenyl-2,6-dimethyl-cyclohex-1-enecarbaldehyde 

Relevant academic research and scientific papers

Total Synthesis of Terpenoids Employing a benzannulation of Carvone Strategy: Synthesis of (-)-Crotogoudin

Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the α-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the ent-3,4-seco-atisane diterpenoid (-)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels-Alder cycloaddition with ethylene gas (to construct the bicyclo[2.2.2]octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of ent-3,4-seco-abietane diterpenoids using an intramolecular oxidative dearomatization.

General diastereoselective synthetic approach toward isospongian diterpenes. Synthesis of (-)-marginatafuran, (-)-marginatone, and (-)-20-acetoxymarginatone

This work describes a synthetic approach to the carbocyclic skeleton of isospongian diterpenes that uses the commercially available monoterpene (S)-carvone as a C-ring synthon, which is incorporated into the tetracyclic isospongian framework via a C→ABC→ABCD ring annulation strategy using intramolecular Diels-Alder and ring-closing metathesis reactions. This approach has been successfully used to prepare both the title natural isospongians and several nonnatural oxygenated analogues. A preliminary evaluation of the inhibitory activity of the small collection of synthesized isospongians on the mammalian mitochondrial respiratory chain revealed that most were able to inhibit the integrated electron transfer chain (NADH oxidase activity) in the micromolar range.

Stereoselective construction of the tetracyclic scalarane skeleton from carvone

The tetracyclic scalarane skeleton 22 has been constructed from (S)-(+)-carvone using two intramolecular Diels-Alder reactions as key synthetic steps.