212185-22-3

Upstream product

• 158930-44-0 6-methyl-carvone 
• 58871-25-3 3-iodopropionaldehyde diethyl acetal 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 74-88-4 methyl iodide 
• 129444-74-2 (5S,6S)-5-Isopropenyl-2,6-dimethyl-cyclohex-2-enone 

Downstream Products

• 225653-29-2 (3S,5R,6R)-6-(3,3-Diethoxy-propyl)-3-hydroxy-5-isopropenyl-2,6-dimethyl-cyclohex-1-enecarbaldehyde 
• 225653-30-5 (1S,4R,5R)-4-(3,3-Diethoxy-propyl)-5-isopropenyl-2,4-dimethyl-3-vinyl-cyclohex-2-enol 
• 225653-31-6 (3R,4R,6S)-3-(3,3-Diethoxy-propyl)-4-isopropenyl-1,3-dimethyl-6-prop-2-ynyloxy-2-vinyl-cyclohexene 
• 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 
• 75657-53-3 stypodiol 
• 182880-82-6 (1aS,1bR,3aR,4S,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol 
• 183072-25-5 (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol 
• 1382088-10-9 C₂₇H₂₇F₅O₄S 
• 1382088-14-3 C₂₈H₂₇F₅O₆S 
• 97640-44-3 isospongia-13,15-dien-20-oic acid 
• 182880-73-5 (5R,6R)-2,6-dimethyl-5-(1-methylethenyl)-6-((E)-4-methyl-5-oxo-3-hexenyl)-2-cyclohexen-1-one 
• 182880-75-7 (5R,6R)-6-[(E)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hexa-3,5-dienyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone 
• 183072-24-4 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal 

Relevant academic research and scientific papers

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.

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.

Diastereoselective synthesis of spongian diterpenes. Total synthesis of the furanoditerpene (-)-spongia-13(16),14-diene

An effective diastereoselective synthesis of the marine-sponge metabolite (-)-spongia-13(16),14-diene 1 is achieved starting from S-(+)- carvone via a homochiral phenanthrenone as the key intermediate for the construction of the furan ring system. S-(+)-C

An efficient stereoselective synthesis of stypodiol and epistypodiol

An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid- catalyzed quinol-tertiary alcohol cyclization as key synthetic steps.