61976-12-3Relevant academic research and scientific papers
Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids
Oberhauser, Clara,Harms, Vanessa,Seidel, Katja,Schr?der, Benjamin,Ekramzadeh, Kimia,Beutel, Sascha,Winkler, Sven,Lauterbach, Lukas,Dickschat, Jeroen S.,Kirschning, Andreas
, p. 11802 - 11806 (2018)
The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.
Synthesis of farnesol analogues containing triazoles in place of isoprenes through 'click chemistry'
Subramanian, Thangaiah,Spielmann, H. Peter,Parkin, Sean
supporting information, p. 2539 - 2543,5 (2012/12/11)
A solid-phase three-component Huisgen reaction has been used to generate polar farnesol and farnesyl diphosphate analogues. The Cu(I)-catalyzed 1,3-cycloadditions of various azides with solid supported (E)-3-methylhept-2-en- 6-yn-1-ol provided only the 1,4-disubstituted 1,2,3-triazole regioisomers. The organic azides were generated in situ to minimize handling of potentially explosive azides. We have employed this powerful click chemistry to make farnesol analogues where both β- and γ-isoprenes were replaced by triazole and substituted aromatic rings, respectively.
General preparation and controlled cyclization of acyclic terpenoids
Kuk, Jinchul,Beom, Soo Kim,Jung, Heejung,Choi, Seyoung,Park, Jung-Youl,Koo, Sangho
, p. 1991 - 1994 (2008/09/18)
A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C5 unit 5 and the chain-termination process utilizing the C5 unit 10 to
Synthesis and confirmation of the structures of polonicumtoxins A, B and C
Yotsu-Yamashita, Mari,Yasumoto, Takeshi,Rawal, Viresh H.
, p. 79 - 93 (2007/10/03)
Total syntheses of polonicumtoxins A (1), B (2), and C (3) have been completed. The key step of the syntheses involves an aza-Wittig reaction for the construction of the cyclic ketimine. The synthetic compounds were found to be identical in all respects with the natural products, thus confirming their assigned structures.
MACRORING CONTRACTION METHODOLOGY. 3. TOTAL SYNTHESES OF COSTUNOLIDE AND HAAGEANOLIDE USING TRANSANNULAR -WITTIG REARRANGEMENT OF 13-MEMBERED DIALLYLIC ETHERS AS KEY REACTION
Takahashi, Takashi,Nemoto, Hisao,Kanda, Yutaka,Tsuji, Jiro,Fukazawa, Yoshimasa,et al.
, p. 5499 - 5520 (2007/10/02)
A new route to construct the carbon skeleton of germacrane sesquiterpenes is described wherein the 13-membered diallylic ethers 12 and 41, prepared by intramolecular O-alkylation of the bromo alcohol and C-alkylation of the cyanohydrin ether respectively,
