2270-72-6Relevant academic research and scientific papers
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 Chiral Pentenolide-Based Unified Strategy toward Dihydrocorynantheal, Dihydrocorynantheol, Protoemetine, Protoemetinol, and Yohimbane
Xie, Changmin,Luo, Jisheng,Zhang, Yan,Zhu, Lili,Hong, Ran
, p. 3592 - 3595 (2017)
An organocatalytic cross-aldol reaction of formaldehyde (formalin) with alkyl aldehydes, followed by the Z-selective Horner-Wadsworth-Emmons (HWE) reaction and immediate lactonization, afforded γ-alkylated pentenolides in good overall yields and excellent
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
Enantioselective synthesis of indoloquinolizidines via asymmetric catalytic hydrogenation/lactamization of imino diesters
Liu, Yong,Wang, Qun,Zhang, Ying,Huang, Jianbiao,Nie, Linlin,Chen, Jie,Cao, Weiguo,Wu, Xiaoyu
, p. 12009 - 12017 (2013)
We have developed a highly efficient cascade sequence for asymmetric synthesis of indoloquinolizidines with absolute control of cis-H2/H12b relative geometry in good to excellent yields and excellent enantioselectivities. This cascade was triggered by the Ru(II)-TsDPEN-catalyzed asymmetric transfer hydrogenation of imino diesters, with subsequent spontaneous lactamization with discrimination between the two diastereotopic 2-alkoxy-2-oxoethyl groups. The synthetic utility of this strategy was demonstrated by the asymmetric preparation of dihydrocorynantheol, geissoschizol, and isogeissoschizol.
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.
Quinolizidines. XXXII. A Chiral Synthesis of 3,4,5,6-Tetradehydro-17-hydroxycorynanium, the Zwitterionic Structure Assigned to an Alkaloid from Aspidosperma marcgravianum
Fujii, Tozo,Ohba, Masashi,Ohashi, Takako
, p. 1879 - 1890 (1993)
The total synthesis of 3,4,5,6-tetradehydro-17-hydroxycorynanium , the zwitterionic structure assigned to an alkaloid from Aspidosperma marcgravianum, has been accomplished for the first time via a "lactim ether route".The route started with initial condensation between the lactim ether and 3-chloroacetylindole and proceeded through the lactam ester , lactam alcohol , acetoxylactam , quaternary iminium salt , and 3,4,5,6-tetradehydro-17-hydroxycorynanium perchlorate .The 1H NMR spectral data and the sign of specific rotation for the synthetic (+)-4 were in disagreement with those reported for a natural sample, leaving the chemistry of this A. marcgravianum alkaloid incomplete.
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
Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine
Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando
, p. 398 - 408 (2012/02/16)
A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences. 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.
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
