2944-47-0Relevant articles and documents
Acid mediated deprotection of N-isopropyl tertiary amides
Lorenc, Chris,Reeves, Jonathan T.,Busacca, Carl A.,Senanayake, Chris H.
, p. 1280 - 1282 (2015)
Tertiary amides containing an N-isopropyl group were selectively deprotected by heating in methanesulfonic acid. The N-isopropyl group was removed selectively in the presence of other groups on the amide nitrogen such as methyl, primary alkyl, or aryl. The putative isopropyl cation was trapped by Friedel-Crafts alkylation of anisole when the latter was included as a co-solvent.
Total Synthesis of 1-Oxomiltirone and Arucadiol
Chai, Uiseong,Kang, Juyeon,Mac, Dinh Hung,Oh, Chang Ho,Seong, Chaehyeon
supporting information, p. 1953 - 1956 (2020/11/24)
A practical and efficient approach for the total synthesis of arucadiol and 1-oxomiltirone is reported. The key step which involves an intramolecular [4+2] cycloaddition catalyzed by gold(III) bromide or copper(II) triflate leads to the formation of 6-6-6-fused aromatic abietane core.
Total synthesis of (±)-Scrodentoid A
Lv, Shao-Dong,Tian, Tian,Zhang, Liu-Qiang,Xu, Si-Yu,Zhao, Dong-Hai,Wang, Jun-Jie,Fu, Jian-Guo,Li, Yi-Ming,Feng, Chen-Guo
, (2019/11/26)
An efficient total synthesis of scrodentoid A was accomplished starting from a Hagemann's ester and a substituted (2-bromoethyl)benzene. Key reactions in this synthesis include C-alkylation of the Hagemann's ester, 6-endo-Trig cationic cyclization of an enone and Lewis acid promoted isomerization of a cis-fused ketone.
Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes
Tao, Zhonglin,Robb, Kevin A.,Zhao, Kuo,Denmark, Scott E.
supporting information, p. 3569 - 3573 (2018/03/21)
A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.
