2270-72-6Relevant articles and documents
Total synthesis of (-)-dihydrocorynantheol using bicyclo[3.2.1]octenone chiral building block
Tosaka, Ayako,Ito, Shinichiro,Miyazawa, Norio,Shibuya, Masatoshi,Ogasawara, Kunio,Iwabuchi, Yoshiharu
, p. 153 - 159 (2006)
The diastereocontrolled synthesis of (-)-dihydrocorynantheol from a bicyclo[3.2.l]octane chiral building block has been achieved by employing a tandem retro-aldol-Pictet-Spengler reaction-C-3 epimerization sequence as the key step.
A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: Efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related
Zhang, Wei,Bah, Juho,Wohlfarth, Andreas,Franzén, Johan
, p. 13814 - 13824 (2011)
Here we present a general and common catalytic asymmetric strategy for the total and formal synthesis of a broad number of optically active natural products from the corynantheine and ipecac alkaloid families, for example, indolo[2,3-a]- and benzo[a]quino
Stereoselective total synthesis of dihydrocorynantheol.
Deiters, Alexander,Martin, Stephen F
, p. 3243 - 3245 (2002)
[reaction: see text] A stereoselective synthesis of the indole alkaloid dihydrocorynantheol (1) from indole-3-acetic acid has been achieved by a sequence involving 9 as a key intermediate. The synthesis of the unsaturated lactam ring in 9 highlights a series of catalytic organometallic reactions featuring two ring-closing metatheses and a zirconocene-catalyzed carbomagnesation. Since no protecting groups were used, the present synthesis of 1 is exceedingly concise, consisting of only eight distinct operations.
Access to electron-rich arene-fused hexahydroquinolizinones through a gold-catalysis-initiated cascade process
Liu, Lianzhu,Zhang, Liming
supporting information; experimental part, p. 7301 - 7304 (2012/09/08)
Golden Cascade: With a tethered, electron-rich arene as the internal nucleophile, a gold-catalyzed amide cyclization to an alkyne initiates a cascade process that ends with a Ferrier rearrangement. Electron-rich arene-bearing hexahydroquinolizin-2-ones are formed in good yields and can be converted into indole alkaloids in only a few steps. Copyright
Organocatalytic approach for the syntheses of corynantheidol, dihydrocorynantheol, protoemetinol, protoemetine, and mitragynine
Sun, Xuefeng,Ma, Dawei
, p. 2158 - 2165 (2011/10/18)
O-Trimethylsilyl (TMS)-protected diphenylprolinol-catalyzed Michael addition of a functionalized alkylidene malonate and n-butanal affords an aldehyde. This adduct can serve as the common intermediate for the assembly of secologanin tryptamine and dopamin