106540-31-2

Upstream product

• 562-13-0 2,2-dimethyl-1,3-cyclohexanedione 
• 61447-86-7 (S)-3-hydroxy-2,2-dimethylcyclohexanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 123427-43-0 (3S)-3-(t-Butyldimethylsiloxy)-6-ethylidene-2,2-dimethylcyclohexanone 
• 139118-53-9 (3S)-3-(t-Butyldimethylsiloxy)-6-(1-hydroxyethyl)-2,2-dimethylcyclohexanone 
• 124177-03-3 (S)-3-(tert-butyldimethylsilyloxy)-6-formyl-2,2-dimethylcyclohexanone 
• 124263-01-0 ethyl (1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneacetate 
• 124177-08-8 ethyl (1R,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneacetate 
• 124177-08-8 ethyl (1R,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneacetate 
• 124263-03-2 (1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneethanol 
• 124177-10-2 (1R,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneethanol 
• 124263-12-3 (1R,1'R,2'R)-1-(3-furyl)-2-(2-'hydroxy-2',6',6'-trimethylcyclohexyl)ethanol 
• 69924-97-6 (1S,1'S,2'S)-1-(3-furyl)-2-(2-'hydroxy-2',6',6'-trimethylcyclohexyl)ethanol 
• 124263-08-7 (1'S,2'S)-1-(3-furyl)-2-(2'-hydroxy-2',6',6'-trimethylcyclohexyl)-1-ethanone 
• 124263-09-8 (1'R,2'R)-1-(3-furyl)-2-(2'-hydroxy-2',6',6'-trimethylcyclohexyl)-1-ethanone 
• 124263-02-1 ethyl (1S,3S)-3-hydroxy-2,2-dimethyl-6-methylenecyclohexaneacetate 
• 124177-09-9 ethyl (1R,3S)-3-hydroxy-2,2-dimethyl-6-methylenecyclohexaneacetate 

Relevant academic research and scientific papers

A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin

We present a full account on the development of the total synthesis of the antiviral meroterpenoid (+)-stachyflin. The decalin subunit is rapidly accessed by an exo-selective Diels–Alder reaction, whereas the isonindolinone was synthesized via a highly efficient and practical de novo route starting from dimedone. A challenging sp2–sp3 Negishi cross-coupling reaction enabled construction of the crucial C15–C16 bond that connects the arene with the decalin subunit. For the final installation of the cis-decalin framework, a Lewis acid-catalyzed cyclization was applied.

Asymmetric synthesis of 3(S),17-dihydroxytanshinone

The first synthesis of 3(S),17-dihydroxytanshinone was achieved by ultrasound promoted Diels-Alder reaction of the protected 3-hydroxymethyl-4,5- benzofurandione with a vinylcyclohexene derivative. Bioassay showed that the synthetic 3(S),17-dihydroxytanshinone was active in vitro against HL-60 tumor cell line by MTT method.

Enantioselective total synthesis of a trans-hydrindane rings/side-chain building-block of vitamin D - Asymmetric induction in an acid-catalyzed conjugate-addition reaction

For the enantioselective total synthesis of 1α,25-dihydroxyvitamin D3 (3), we have developed an enantioselective approach to the "northern" portion building-block 8, starting from the optically active hexanoic acid derivative 44, 2-methylcyclopent-2-en-1-one (10) and 1-(phenylthio)but-3-en-2-one (9). The steric course of the addition reaction of homochiral (S)-ketene acetals 28, 40, 44 and 58 with 10 was examined. We found that in the cases of 28, 44 and 40, the reactions occur with high simple and induced (facial) diastereoselectivities. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.