Gram-Scale Total Synthesis of Carbazomycins A–D through Late-Stage Regioselective Demethylation of Aryl Methyl Ethers DOI

Yuxuan Feng,

Atsunori Mori, Kentaro Okano

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13472 - 13484

Published: Sept. 5, 2024

Gram-scale total synthesis of carbazomycins A-D is described. The carbazomycin A was achieved in 44% overall yield over six steps from symmetrical 5-chloro-1,2,3-trimethoxybenzene. key aryne-mediated carbazole formation and methylation provided the multiply substituted carbazole. regioselective demethylation trimethoxycarbazole performed using boron trichloride. Thereafter, phenolic hydroxy group converted into methyl to provide A. Subsequent installation methoxy realized D. Regioselective 1-dodecanethiol, effecting conversions D B C, respectively.

Language: Английский

Synthesis of pyrazolo[1,2-a]cinnolinone via copper-catalyzed 6-endo-dig cyclization DOI
Cong Zhang, Zhang Wen,

Yangang Wu

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134593 - 134593

Published: March 1, 2025

Citations

0
Gram-Scale Total Synthesis of Carbazomycins A–D through Late-Stage Regioselective Demethylation of Aryl Methyl Ethers DOI

Yuxuan Feng,

Atsunori Mori, Kentaro Okano

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13472 - 13484

Published: Sept. 5, 2024

Gram-scale total synthesis of carbazomycins A-D is described. The carbazomycin A was achieved in 44% overall yield over six steps from symmetrical 5-chloro-1,2,3-trimethoxybenzene. key aryne-mediated carbazole formation and methylation provided the multiply substituted carbazole. regioselective demethylation trimethoxycarbazole performed using boron trichloride. Thereafter, phenolic hydroxy group converted into methyl to provide A. Subsequent installation methoxy realized D. Regioselective 1-dodecanethiol, effecting conversions D B C, respectively.

Language: Английский

Citations

0