7171-78-0Relevant academic research and scientific papers
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
, 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.
RING CLEAVAGE AND RECONSTRUCTION OF FIVE AND SIX MEMBERED RING
Suemune, Hiroshi,Oda, Kozo,Sakai, Kiyoshi
, p. 3373 - 3376 (2007/10/02)
Under the acetalization conditions using BF3-etherate/ethylene glycol, cyclopentanones and cyclohexanones with the carbonyl function at the C3- or C4-position of the β-side chain undergo the facile ring cleavage to reconstruct the new ring.
