72453-33-9Relevant academic research and scientific papers
A general method for the highly diastereoselective, kinetically controlled alkylation of ( )-nopinone
Campos, Kevin R,Lee, Sandra,Journet, Michel,Kowal, Jason J,Cai, Dongwei,Larsen, Robert D,Reider, Paul J
, p. 6957 - 6959 (2007/10/05)
A general method for the monoalkylation of (+)-nopinone was developed for a variety of carbon and heteroatom electrophiles to afford the kinetically controlled product 2 with high diastereoselectivity (98% d.e.) and excellent yield (75-90%).
(13)C magnetic resonance studies. 124. Preparative ring expansions of bicyclic ketones by homoketonization of cylopropoxide analogs
Patel, Vijay,Ragauskas, Arthur J.,Stothers, J. B.
, p. 1440 - 1449 (2007/10/02)
Homoketonization of some readily prepared cyclopropoxides provides a new synthetic method for ring expansion of the and ring systems.Cyclopropanation of the trimethylsilyl enol ethers derived from a variety of polycyclic ketones affords the required cyclopropyl silyl ethers, which may be ketonized directly or hydrolyzed to the corresponding cyclopropanols before ketonization.The results for fourteen examples serve to define the scope of the ring expansion process, and the silyl enol ethers, cyclopropyl silyl ethers, and most of the corresponding cyclopropanols have been characterized by (13)Cmr.The stereochemistry of the ketonization leading to ring expansion has been established by deuterium labelling experiments.
Synthetic Study of (+)-Nootkatone from (-)-β-Pinene
Yanami, Tetsuji,Miyashita, Masaaki,Yoshikoshi, Akira
, p. 607 - 612 (2007/10/02)
A facile stereoselective synthesis of (+)-nootkatone (1) has been achieved starting with (+)-nopinone (2b).The key step was the conjugate addition of methallyltrimethylsilane (20b) to trans-3-ethylidenenopinone (16), which was obtainable from 2b on the cross condensation with acetaldehyde followed by acid treatment, giving an adduct with the desired stereochemistry, 24a, as the predominant product.Dione 23, obtained from the adduct on methylation followed by ozonization, afforded nootkatone hydrochloride (26) on treatment with hydrogen chloride.Regioselective dehydrochlorination of the hydrochloride yielded 1.An alternative route in which allyltrimethylsilane was used is also described.
