143459-20-5Relevant academic research and scientific papers
Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol
Jung, Michael E.,Im, G-Yoon J.
, p. 4962 - 4964 (2008)
The convergent total synthesis of the HIF-1 inhibitor laurenditerpenol 1a is reported. The key step is the Julia olefination-reduction process between the two components, the sulfone 4 (prepared from the dimethylfuran-maleic anhydride Diels-Alder adduct)
Stereoselective Total Synthesis of (±)-Pleurospiroketals A and B
Thorat, Sagar S.,Rama Krishna, Gamidi,Kontham, Ravindar
, p. 13572 - 13582 (2021/10/12)
A full account of our efforts toward the stereoselective total synthesis of sesquiterpenoid-derived natural products (±)-pleurospiroketals A and B is described. Commercially available 3-methyl-2-cyclohexenone and 2,2-dimethyloxirane were used as key build
Construction of Morphan Derivatives by Nitroso–Ene Cyclization: Mechanistic Insight and Total Synthesis of (±)-Kopsone
Zhai, Li,Tian, Xuechao,Wang, Chao,Cui, Qi,Li, Wenhua,Huang, Sha-Hua,Yu, Zhi-Xiang,Hong, Ran
supporting information, p. 11599 - 11603 (2017/09/11)
A type II nitroso–ene cyclization was developed for the construction of morphan derivatives with good functional-group tolerance. DFT calculations revealed that the nitroso–ene reaction proceeds in a stepwise manner involving diradical or zwitterionic intermediates. The rate-determining step is C?N bond formation, followed by a rapid hydrogen-transfer step with a chair-conformation transition state. The current approach was also successfully applied in the first total synthesis of (±)-kopsone, a highly strained yet simple morphan-type alkaloid isolated from Kopsia macrophylla.
Total synthesis of racemic laurenditerpenol, an HIF-1 inhibitor
Jung, Michael E.,Im, G.-Yoon Jamie
experimental part, p. 8739 - 8753 (2010/03/04)
(Figure Presented) The convergent total synthesis of the HIF-1 inhibitor laurenditerpenol 1 and its diastereomer 1′ is reported. The key step involves the Julia-Kocienski olefination-reduction process between the sulfone 55 and the aldehyde 54. The unusual trimethylated oxanorbornane sulfone 55 was successfully synthesized from the known exo Diels-Alder adduct 24 of 2,5-dimethylfuran 7 and maleic anhydride 23 in 8 steps. The aldehyde 54 was prepared by ring-opening and elaboration of lactone 41. In addition, four analogues of 1 were also successfully synthesized for biological testing.
