Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Propargyl Chlorides and Carbonates
Palladium(0)-catalyzed cyclization of bromoallenes, propargyl chlorides, and carbonates bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. Cyclization reactivity is dependent on the relative configuration of the benzamide and leav...
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| Veröffentlicht in: | Journal of organic chemistry 2010-06, Vol.75 (11), p.3831-3842 |
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| container_end_page | 3842 |
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| container_issue | 11 |
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| container_title | Journal of organic chemistry |
| container_volume | 75 |
| creator | Inuki, Shinsuke Yoshimitsu, Yuji Oishi, Shinya Fujii, Nobutaka Ohno, Hiroaki |
| description | Palladium(0)-catalyzed cyclization of bromoallenes, propargyl chlorides, and carbonates bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. Cyclization reactivity is dependent on the relative configuration of the benzamide and leaving groups, and on the nature of the leaving groups. This bis-cyclization was used as the key step in a short total synthesis of pachastrissamine, which is a biologically active marine natural product. |
| doi_str_mv | 10.1021/jo100544v |
| format | Article |
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| ispartof | Journal of organic chemistry, 2010-06, Vol.75 (11), p.3831-3842 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| subjects | Alkynes - chemistry Carbonates - chemistry Catalysis Chemical reactivity Chemistry Chlorides - chemistry Cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Palladium - chemistry Preparations and properties Reactivity and mechanisms Sphingosine - analogs & derivatives Sphingosine - chemical synthesis Stereoisomerism |
| title | Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Propargyl Chlorides and Carbonates |
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