109028-15-1Relevant academic research and scientific papers
Preparation and use of enantioenriched 2-aryl-propylsulfonylbenzene derivatives as valuable building blocks for the enantioselective synthesis of bisabolane sesquiterpenes
Serra, Stefano
, p. 1561 - 1572 (2015/02/05)
We have demonstrated that different enantioenriched 2-arylpropylsufonylbenzene derivatives are very useful building blocks for the synthesis of aromatic bisabolane sesquiterpenes. Their preparation and the exploitation of their chemical reactivity have been comprehensively investigated. Accordingly, the naturally occurring bisabolane sesquiterpenes (-)-curcuphenol, (-)-xanthorrhizol, (+)-glandulone A, (+)-curcudiol, (+)-turmerone and (+)-curcudiol-10-one were synthesized in high enantiomeric purity. It is worth noting that the compounds (+)-curcudiol-10-one and (+)-glandulone A were prepared in enantioenriched form for the first time. Through the proposed synthetic approaches, we were able to confirm both chemical structures and the absolute configurations previously assigned to the two aforementioned sesquiterpenes.
Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: Highly enantioselective and chemoselective access to a chiral benzylmethyl center
Yang, Shuang,Zhu, Shou-Fei,Guo, Na,Song, Song,Zhou, Qi-Lin
, p. 2049 - 2052 (2014/03/21)
A carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins was developed by using a chiral spiro iridium catalyst, providing a highly efficient approach to the compounds with a chiral benzylmethyl center. The carboxy-directed hydrogenation prohibited the isomerization of the terminal olefins, and realized the chemoselective hydrogenation of various dienes. The concise enantioselective syntheses of (S)-curcudiol and (S)-curcumene were achieved by using this catalytic asymmetric hydrogenation as a key step.
Total synthesis and repudiation of the helianane family
Green, Jason C.,Jimenez-Alonso, Sandra,Brown, Eric. R.,Pettus, Thomas R. R.
supporting information; experimental part, p. 5500 - 5503 (2011/12/22)
Total syntheses of two structures purported as (+)-heliananes were completed in six pots. Spectral comparisons, between the synthetic and natural compounds, revealed a misassignment of the eight-membered ring in the heliananes. The key step in the synthes
Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol1)
Ono,Ogura,Hatogai,Akita
, p. 1581 - 1585 (2007/10/03)
A highly enantioselective synthesis of the versatile chiral synthons possessing one stereogenic center, (S)-and (R)-4-aryl-5-hydroxy-(2E)-pentenoate (3) was achieved based on the enzymatic reaction of (±)-3 with commercially available lipases MY-30 or OF-360 from Candida rugosa. Application of (S)-3 and (R)-3 to the total syntheses of (S)-curcuphenol (1), (S)-curcudiol (2), and (R)-curcuphenol (1), respectively, is described.
Enantioselective construction and utilization of 2-(cyclohex-2-enyl)phenols
Konno, Hiroyuki,Ogasawara, Kunio
, p. 1004 - 1006 (2007/10/03)
Enantioselective construction of 2-(cyclohex-2-enyl)phenols from chiral equivalents of cyclohex-2-enols has been investigated by employing a concurrent retro-Diels-Alder reaction and Claisen rearrangement protocol. Utilizing the enantiomerically pure product obtained, the first enantiocontrolled synthesis of a phenolic natural sesquiterpene (+)-curcudiol, isolated from the marine sponge Didiscus flavus, has been demonstrated.
Total Synthesis of (S)-(+)-Curcudiol, (S)- and (R)-(-)-Curcuphenol Based on Enzymatic Resolution of a Primary Alcohol Possessing One Stereogenic Center
Ono, Machiko,Ogura, Yuuko,Hatogai, Kazumi,Akita, Hiroyuki
, p. 1829 - 1832 (2007/10/03)
A highly stereoselective synthesis of the versatile chiral synthons possessing one stereogenic center, (S)-3 and (R)-3 was achieved and the application of (S)-3 and (R)-3 into the total syntheses of (S)-curcuphenol (1), (S)-curcudiol (2), and (R)-curcuphenol (1), respectively, was described.
