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
Convenient synthesis of the key intermediate for dihydrocorynantheol and protoemetinol from the monoacetate of 4-cyclopentene-1,3-diol
Kobayashi, Yuichi,Yagi, Kaori,Kaneko, Yuki
, p. 1541 - 1548 (2011/05/05)
We invented an efficient method to obtain the key δ-lactone possessing the (CH2)2OTBDPS and Et groups at C3 and C4, respectively, starting with the acetate of 4-cyclopentene-1,3-diol, which was subjected to Pd-catalyzed allylation with malonate anion to attach the (CH 2)2OTBDPS group. The Et group was then installed by 1,4-addition to the derived enone. Finally, the resulting enol TMS ether was oxidized to afford the lactone. Furthermore, the lactone was converted to dihydrocorynantheol and protoemetinol, both of which are typical examples of indoloquinolizidine and benzo[α]quinolizine alkaloids. The Japan Institute of Heterocyclic Chemistry.