2020
DOI: 10.1002/ejoc.202000459
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Total Synthesis of the Antitumor Depsipeptide FE399 and Its S‐Benzyl Derivative: A Macrolactamization Approach

Abstract: An efficient and practical method for the synthesis of (9R,14R,17R)‐FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2‐methyl‐6‐nitrobenzoic anhydride (MNBA)‐mediated dehydration condensation reaction was effectively employed for the formation of the 16‐membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S‐benzyl product and isolated as a sin… Show more

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Cited by 6 publications
(10 citation statements)
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References 26 publications
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“…Moreover, we have already determined that the combination of MNBA and DMAPO, a weaker base than DMAP, is effective as a coupling reagent for lactam formation. 9 In fact, on using DMAPO as a nucleophilic catalyst instead of DMAP, the target product was efficiently obtained, as is the case with DMAP (entry 8). Specifically, in the presence of MNBA (1.3 equiv) combined with the catalytic amount of DMAPO (0.2 equiv) and triethylamine (2.6 equiv), the best yield of 11 was obtained through MNBA-mediated macrolactamization (entry 9).…”
Section: ■ Results and Discussionmentioning
confidence: 95%
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“…Moreover, we have already determined that the combination of MNBA and DMAPO, a weaker base than DMAP, is effective as a coupling reagent for lactam formation. 9 In fact, on using DMAPO as a nucleophilic catalyst instead of DMAP, the target product was efficiently obtained, as is the case with DMAP (entry 8). Specifically, in the presence of MNBA (1.3 equiv) combined with the catalytic amount of DMAPO (0.2 equiv) and triethylamine (2.6 equiv), the best yield of 11 was obtained through MNBA-mediated macrolactamization (entry 9).…”
Section: ■ Results and Discussionmentioning
confidence: 95%
“…On the basis of our previous result 9 on the use of macrolactamization for the FE399 synthesis, we were interested to determine to what extent MNBA should promote target macrolactamization compared to conventional coupling reagents for amide and peptide bond formation. Thus, we evaluated the efficacy of the target macrolactamization of ring-closing precursor 10 using MNBA combined with DMAPO or DMAP as coupling reagents (Table 1).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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