863662-92-4Relevant academic research and scientific papers
Synthetic versatility in C-H oxidation: A rapid approach to differentiated diols and pyrans from simple olefins
Gormisky, Paul E.,White, M. Christina
, p. 12584 - 12589 (2011/10/05)
Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiated syn-1,2-diols, stereodefined amino-polyols, and syn-pyrans, structures ubiquitous in medicinally important complex molecules found in Nature. We also demonstrate that a C-H oxidation approach to the synthesis of these motifs is orthogonal and complementary to other state-of-the-art methods.
Assignment of absolute configuration to SCH 351448 via total synthesis
Cheung, Lael L.,Marumoto, Shinji,Anderson, Christopher D.,Rychnovsky, Scott D.
supporting information; experimental part, p. 3101 - 3104 (2009/05/07)
(Chemical Equation Presented) The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule.
Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations
Kang, Eun Joo,Cho, Eun Jin,Ji, Mi Kyung,Lee, Young Eun,Shin, Dong Mok,Choi, Soo Young,Chung, Young Keun,Kim, Jong-Seo,Kim, Hie-Joon,Lee, Sueg-Geun,Lah, Myoung Soo,Lee, Eun
, p. 6321 - 6329 (2007/10/03)
(+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia-Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical cyclization reactions of β-alkoxyacrylates. Analogous SCH 351448 salts incorporating other mono- and divalent cations may be prepared. Under acidic conditions, SCH 351448 (Na+ salt A) was the most stable complex, but SCH 351448 (Ca2+ salt) and (Na+ salt B) appear to be physiologically important species.
Total Synthesis of (+)-SCH 351448
Kang, Eun Joo,Cho, Eun Jin,Lee, Young Eun,Ji, Mi Kyung,Shin, Dong Mok,Chung, Young Keun,Lee, Eun
, p. 2680 - 2681 (2007/10/03)
Total synthesis of SCH 351448 was accomplished employing the ring-closing olefin metathesis reaction for the preparation of the 28-membered macrodiolide. Copyright
