176774-92-8

Upstream product

• 50-00-0 formaldehyd 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 

Downstream Products

• 935264-81-6 (4E,7S)-N-{(2R)-[(1R,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 935264-77-0 (4E,7S)-N-{(2S)-[(1R,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 935264-82-7 (4E,7S)-N-{(2R)-[(1R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 935264-78-1 (4E,7S)-N-{(2S)-[(1R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide 
• 935264-69-0 [(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane 
• 935264-86-1 (1R)-1-[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-nitroethan-1-ol 
• 935264-74-7 (1S)-1-[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-nitroethan-1-ol 
• 935264-66-7 (1S,3S,4R,5R,6S)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate 
• 935264-80-5 {(1S,5R,6R)-6-[(1R)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane 
• 935264-57-6 {(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane 
• 935264-63-4 {(1S,2R,3S,4S,6S)-2-(4-methoxybenzyloxy)-1-methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptan-3-yl}methoxy(1,1-dimethylethyl)dimethylsilane 
• 935264-65-6 1-{(1S,3S,4S,5R,6S)-4-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl}ethan-1-one 
• 935264-67-8 (1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate 
• 935264-71-4 [(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methanol 

Relevant academic research and scientific papers

Studies towards Simalikalactone D and Quassimarin: Construction of an Advanced Pentacyclic Intermediate

An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)-(+)-carvone in 21 steps and with an overall yield of 12%. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a 1,3-sigmatropic rearrangement and an intramolecular Diels-Alder reaction as the key steps.

Total synthesis and correct absolute configuration of malyngamide U

The enantioselective synthesis of the previously proposed structure of malyngamide U (1) was accomplished in 18 steps from (S)-(+)-carvone. The key steps involved a hydroxymethylation of (S)-(+)-carvone and an asymmetric Henry reaction of aldehyde (+)-5,