- Total Synthesis of Laucysteinamide A, a Monomeric Congener of Somocystinamide A
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Laucysteinamide A (4) is a marine natural product isolated from the cyanobacterium Caldora penicillata and contains structural motifs found in promising cancer drug leads. The first total synthesis of 4 and its analogues was achieved, which also enabled a concise formal synthesis of somocystinamide A (3), a dimeric congener of 4 that previously showed extremely potent antiproliferative activities. This work provides further insights on structure-activity relationships in this class of natural products.
- Taylor, Kimberly S.,Zhang, Chen,Glukhov, Evgenia,Gerwick, William H.,Suyama, Takashi L.
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supporting information
p. 865 - 870
(2021/04/02)
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- A natural ɑ - glucosidase inhibitor Penasulfate A synthetic method (by machine translation)
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The invention provides a natural ɑ - glucosidase inhibitor Penasulfate A synthetic method, including by the 1, 12 - dodecanediol via 5 step synthesis 12 - thirteen carbon olefine acid, L - arabinose via the 3 step synthesis (2 S, 3 R) - 2, 3 - oxygen - isopropyl - 4 - pentene - 1, 2, 3 - triol, (S)- Roche ester via the 8 step synthesis of chiral methyl undecenyl fundamental frequency that mellow boron ester, 12 - thirteen alkenylene acid and (2 S, 3 R) - 2, 3 - oxygen - isopropyl - 4 - pentene - 1, 2, 3 - triol in GrubbsII catalyst under the action of the olefin metathesis reaction, and then with the (R)- piperidine - 2 - carboxylic acid methyl ester reaction to prepare amide, re-oxidation results in the aldehyde, Takai alkene alkylation by thirteen alkenylene iodide, with the insecticidal compositions of the fundamental frequency that chiral methyl mellow boron ester in Pd (PPh3 )4 Catalytic, ethyl alcohol thallium as alkali under the condition of the key Suzuki coupling, hydrogenation reduction, [...], sulfuric acid ester, shall Penasulfate A. The present invention provides natural product Penasulfate A throughout the synthetic route for the first time, the olefin metathesis reactions and Suzuki coupling as a key reaction, the line is comparatively simple high efficiency, a high degree of convergence, the operation is easy to grasp. (by machine translation)
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- Total Synthesis of the Proposed Structure of Penasulfate A: L -Arabinose as a Source of Chirality
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The total synthesis of putative penasulfate A was effectively achieved by a convergent strategy with a longest linear sequence of 14 steps and overall yield of 8.6%. The highlights of our strategy involved an E-selective olefin cross-metathesis, Suzuki cross-coupling, and a copper(I)-catalyzed coupling reaction.
- Gao, Yangguang,Cao, Zhou,Zhang, Qiang,Guo, Rui,Ding, Fei,You, Qingliang,Bi, Jingjing,Zhang, Yongmin
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p. 1908 - 1916
(2019/08/20)
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- Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes
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The biocatalytic oxidative tandem decarboxylation of C7–C18dicarboxylic acids to terminal C5–C16dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene; scale-up allowed the isolation of 1,15-hexadecadiene and 1,11-dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.
- Dennig, Alexander,Kurakin, Sara,Kuhn, Miriam,Dordic, Andela,Hall, Mélanie,Faber, Kurt
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supporting information
p. 3473 - 3477
(2016/07/29)
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- Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole side-chain and macrocyclic ring closure
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A synthetic approach to a new class of microtubule-stabilizing natural products is described which employs a macrocyclic olefination strategy to cyclize the 16-membered lactone ring. The C13-C19 thiazole subunit of epothilone A and B is prepared in high enantioselectivity using a catalytic asymmetric allylation reaction.
- Taylor, Richard E.,Haley, Jeffrey D.
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p. 2061 - 2064
(2007/10/03)
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