76909-91-6Relevant academic research and scientific papers
Total synthesis of carbocyclic analogues of coformycin
Saville-Stones, Elizabeth A.,Turner, Richard M.,Lindell, Stephen D.,Jennings, Neil S.,Head, John C.,Carver, David S.
, p. 6695 - 6704 (1994)
Four carbocyclic analogues of the ribonucleoside coformycin, including the recently isolated natural product 2, have been synthesized in racemic form. The syntheses were achieved in a convergent and direct manner via palladium(0) catalysed coupling between diazepinones 15 and 16 and the allylic acetate 5.
Total Synthesis of Prostratin, a Bioactive Tigliane Diterpenoid: Access to Multi-Stereocenter Cyclohexanes from a Phenol
Ding, You-Song,Ding, Zhengwei,Li, Pengfei,Liu, Zhi,Tong, Guanghu,Xu, Liang,Zhang, Hailong
, p. 4813 - 4837 (2020/05/01)
Tiglianes such as prostratin and related diterpenoids are biologically significant natural molecules and long-standing targets for organic synthesis community. Due to the complex polycyclic scaffolds, high oxygenation level, and dense functional groups and stereocenters, their de novo chemical syntheses still face formidable challenges despite extensive efforts in the past 40 years. This account details the development of a modular and concise synthesis of prostratin, a potent anti-HIV and anticancer agent. The key approach in this synthesis involved a sequence of oxidative dearomatization and sequential stereoselective installation of peripheral groups to rapidly build the contiguously substituted cyclohexane C-ring. Inspired by Wender's work, an acid- A nd solvent-controlled stereodivergent formation of cyclopropane D-ring was developed. Mechanistic investigations by computational methods revealed that the competition between intra- A nd intermolecular hydrogen bonding led to different conformations, thus favoring different protonation processes. The designed and unexpected chemistry along this campaign reflected the uniqueness of the natural structures and should be amenable to future chemical syntheses of related complex polycyclic molecules.
Synthesis and evaluation of cis-1-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-5- [124I]iodouracil: A new potential PET imaging agent for HSV1-tk expression
Ahn, Hyunseok,Tae, Hyun Choi,De Castro, Kathlia,Kyo, Chul Lee,Kim, Byoungsoo,Byung, Seok Moon,Su, Hee Hong,Jong, Chan Lee,Kwon, Soo Chun,Gi, Jeong Cheon,Sang, Moo Lim,Gwang, Il An,Rhee, Hakjune
, p. 6032 - 6038 (2008/04/12)
In our pursuit to find an appropriate reporter probe for herpes simplex virus type-1 thymidine kinase (HSV1-tk), a carbocyclic nucleoside analogue, cis-1-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-5-[124I]iodouracil, has been efficiently synthesize
SYNTHESIS OF 9-(C-5-HYDROXY-C-4-HYDROXYMETHYLCYCLOPENT-2-EN-R-1-YL)-9H-ADENINE
Toyota, Akemi,Katagiri, Nobuya,Kaneko, Chikara
, p. 27 - 30 (2007/10/02)
9-(c-5-Hydroxy-c-4-hydroxymethylcyclopent-2-en-r-1-yl)-9H-adenine has been synthesized from the bicyclic hydroxylactone (2) in eleven steps.
A short and stereoselective synthesis of (±)-aristeromycin
Hutchison,Grim,Chen
, p. 451 - 452 (2007/10/02)
A new stereoselective three-step total synthesis of (±)-aristeromycin starting from readily available 1-hydroxymethyl-3-cyclopentene is described.
Deamination Reactions, 49. - Decomposition of 2-Oxa-5- and -6-norbornanediazonium Ions
Kirmse, Wolfgang,Mrotzeck, Uwe
, p. 485 - 492 (2007/10/02)
The reactivity of 2-oxa-6-norbornanediazonium ions (19, 20) conforms to that of the analogous brosylates (7, 11).Photolysis of the tosylhydrazone 17 in aqueous sodium hydroxide yields 2-oxa-exo-6-norbornanol (15) with no endo isomer 22.The deuterium incor
Cyclit-Reaktionen, II. Darstellung von Bausteinen zur Synthese carbocyclischer Furanose-Analoga
Paulsen, Hans,Maass, Uwe
, p. 346 - 358 (2007/10/02)
The four isomeric hydroxycyclopentenmethanols 6a to 9a can easily be made by allylhydroxylation of the epoxides 2 and 4 with phenyl selenide.In a second way the pair 8a and 9a has been synthesized from 11 via 15.As the preparation of 20 demonstrates, the functionalisation of 6a to 9a to carbocyclic furanoses is possible.The dicarboxylic diethyl esters 23 and 33 can be converted into models for carbocyclic ketofuranoses.
