191410-00-1

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 158252-77-8 (2R,3R,5R)-3-hydroxy-2-methyl-5-(1-methylethenyl)cyclohexanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 6485-40-1 (R)-Carvone 
• 36616-60-1 (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 

Downstream Products

• 1309930-37-7 (5R,6R)-5-tert-butyldimethylsilyloxy-6-methyl-2-cyclohexenone 
• 1309930-42-4 (5R,6R)-5-tert-butyldimethylsilyloxy-2-iodo-6-methyl-2-cyclohexenone 
• 1309930-44-6 (1R,5R,6S)-5-tert-butyldimethylsilyloxy-2-iodo-6-methylcyclohex-2-enol 
• 1309930-46-8 [(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane 
• 485388-83-8 (4E,7S)-N-{(2R)-2-[(4R,5R)-4-hydroxy-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 1309930-36-6 N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione 
• 1309930-49-1 2-{[(2R,4S,7R,8S,8aR)-7-(tert-butyldimethylsilyloxy)-8-methyl-2-phenyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-4-yl]methyl}-isoindoline-1,3-dione 
• 1309930-51-5 (4E,7S)-N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide 
• 1309930-52-6 2-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-methoxyethyl}-isoindoline-1,3-dione 
• 1309930-54-8 (4E,7S)-N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-cyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 1309930-55-9 (4E,7S)-N-{(2S)-2-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-methyl-6-oxocyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 1309930-56-0 (4E,7S)-N-{2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-oxoethyl}-7-methoxydodec-4-enamide 
• 1309930-59-3 (4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl]-2-hydroxyethyl}-7-methoxydodec-4-enamide 
• 1309930-61-7 (4E,7S)-N-{(2R)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-cyclohex-1-enyl]-2-methoxyethyl}-7-methoxydodec-4-enamide 

Relevant academic research and scientific papers

Total synthesis and absolute configuration of malyngamide W

A concise enantioselective synthesis of malyngamide W (1) and its 2′-epimer was described. The strategy was based on three key steps: (1) ozonolysis of compound 11 which was derived from (R)-(-)-carvone 8, followed by copper-iron-catalyzed rearrangement to give the key cyclohex-2-enone intermediate 5, (2) Nozaki-Hiyama-Kishi coupling reaction between aldehyde 4 and iodide 14 to afford alcohol 3, and (3) asymmetric (R)-CBS reduction of the ketone functionality in compound 21 to establish the C-2′ chiral center in the target compound 1. The absolute configuration of malyngamide W (1) was thus confirmed via the synthesis of 1 and 2′-epi-1.

Bryostatin: A novel asymmetric synthesis of the C27-C34 fragment starting from (R)-carvone as chiral template

(R)-Carvone is a suitable chiral template for the synthesis of differently protected (4S,6R,7R)-trihydroxy-1-octyne derivatives, the C27-C34 fragment of bryostatins. Also other potentially interesting chiral building blocks are described.

(R)-Carvone as chiral template for the synthesis of some polyols

Some (4S,6R,7R) 4,6,7-trihydroxyheptyl derived building blocks have been obtained from (R)-carvone as the chiral template.A key-step is the Baeyer-Villiger oxidation of a suitable intermediate.