114198-58-2Relevant academic research and scientific papers
Synthesis of a diterpene taxoid skeleton, bicyclo[9.3.1]pentadecatriene
Shibuya, Satoshi,Isobe, Minoru
, p. 6677 - 6698 (1998)
The synthesis of bicyclo[9.3.1]pentadecatriene skeleton was investigated by employing cyclization reactions using two key precursors bearing acetylene cobalt complex. Cyclization for the synthesis of strained twelve-membered ring was achieved via Nicholas type reaction in reasonable yield. Reductive decomplexation of the dicobalt hexacarbonyl moiety of the cyclization product was achieved with n-Bu3SnH in the presence of a catalytic amount of NBS in 1,4-cyclohexadiene solvent.
Total Synthesis of 1-Hydroxytaxinine
Imamura, Yusuke,Yoshioka, Shun,Nagatomo, Masanori,Inoue, Masayuki
, p. 12159 - 12163 (2019/08/02)
1-Hydroxytaxinine (1) is a cytotoxic taxane diterpenoid. Its central eight-membered B-ring possesses four oxygen-functionalized centers (C1, C2, C9, and C10) and two quaternary carbon centers (C8 and C15), and is fused with six-membered A- and C-rings. The densely functionalized and intricately fused structure of 1 makes it a highly challenging synthetic target. Reported here is an efficient radical-based strategy for assembling 1 from A- and C-ring fragments. The A-ring bearing an α-alkoxyacyl telluride moiety underwent intermolecular coupling with the C-ring fragment by a Et3B/O2-promoted decarbonylative radical formation. After construction of the C8-quaternary stereocenter, a pinacol coupling reaction using a low-valent titanium reagent formed the B-ring with stereoselective installation of the C1,C2-diol. Subsequent manipulations at the A- and C-rings furnished 1 in 26 total steps.
NRF 2 ACTIVATOR
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, (2018/08/20)
Provided are compounds of Formula I, or pharmaceutically acceptable salts thereof, which are activators of nuclear factor erythroid 2 (NF-E2) -related factor 2 (Nrf2) and are useful to treat diseases caused by oxidative stress, such as neurodegenerative diseases or inflammation. Also provided are methods for their use and production.
A concise enantioselective synthesis of a fully oxygen substituted ring A taxol precursor
Roy, Olivier,Pattenden, Gerald,Pryde, David C.,Wilson, Claire
, p. 5115 - 5121 (2007/10/03)
A concise synthesis of the oxygen substituted ring A compound 2 found in Taxol 1a and Taxotere 1b starting from 2,2-dimethylcyclohexane-1,3-dione and proceeding via the key intermediates 8 and 11, is described. The absolute configuration of 2 was established from an X-ray crystal structure determination of a 4-bromophenylbenzoate derivative, viz. 15.
