- Enantioselective Synthesis of (+)-Mitomycin K by a Palladium-Catalyzed Oxidative Tandem Cyclization
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The mitomycins, a family of bioactive natural products, feature a compact 6/5/5-fused polycyclic ring structure densely decorated with highly reactive and/or fragile quinone, amino ketal, and aziridine as well as carbamate moieties. It is this striking feature that has defeated numerous synthetic attempts towards these apparently small molecules, rendering them one of the most formidable targets for total synthesis. We herein report the first enantioselective synthesis of (+)-mitomycin K, a representative of G series mitomycins. The key step of this synthesis is an enantioselective oxidative cyclization catalyzed by a palladium/(+)-sparteine system that had previously been developed by our group. The robustness of this method bodes well for further applications in the asymmetric total synthesis of natural products, particularly those with characteristic 6/5/5-fused pyrroloindole skeletons.
- Gu, Qiang-Shuai,Yang, Dan
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supporting information
p. 5886 - 5889
(2017/05/12)
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- Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation
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A connective Pummerer-type cyclisation involving a cysteine derivative and an N-benzyl glyoxamide 3 has been applied in an asymmetric synthesis of the protected ABH rings 2 of the antitumour and antimicrobial natural product ecteinascidin 597.
- Smith, Laura H. S.,Nguyen, Trung Thanh,Sneddon, Helen F.,Procter, David J.
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supporting information; experimental part
p. 10821 - 10823
(2011/11/05)
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- Studies directed to the total synthesis of ET 743 and analogues thereof: An expeditious route to the ABFGH subunit
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(matrix presented) In model studies directed to the total synthesis of Et743, a strategic S-C bond formation in systems 26 and 27 was demonstrated. It was further shown that Pictet-Spengler cyclization leading to spiro product 33 exhibits very high stereo
- Zhou, Bishan,Guo, Jinsong,Danishefsky, Samuel J.
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