Asymmetric Total Syntheses of (–)-Dihydromaritidine and (–)-Oxomaritidine

Abhinay Yadav; Satyajit Majumder; Mrinal Kanti Das; Ayan Mondal; Alakesh Bisai

doi:10.1055/a-1912-2378

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(07): 858-862
DOI: 10.1055/a-1912-2378

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Chemical Synthesis and Catalysis in India

Asymmetric Total Syntheses of (–)-Dihydromaritidine and (–)-Oxomaritidine

Abhinay Yadav‡

^aDepartment of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal–462 066, Madhya Pradesh, India

,

Satyajit Majumder‡

^aDepartment of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal–462 066, Madhya Pradesh, India

,

Mrinal Kanti Das

^bDepartment of Chemistry, Karimpur Pannadevi College, University of Kalyani, Nadia–741 152, West Bengal, India

,

Ayan Mondal

^cDepartment of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia–741 246, West Bengal, India

,

Alakesh Bisai∗

^aDepartment of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal–462 066, Madhya Pradesh, India

^cDepartment of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia–741 246, West Bengal, India

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Abstract

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Abstract

A concise catalytic asymmetric approach to naturally occurring Amaryllidaceae alkaloids sharing a 5,10b-ethanophenanthridine skeleton [(–)-oxomaritidine, (–)-dihydromaritidine, (–)-maritidine, and (–)-epi-maritidine] has been envisioned. The key intermediate in this strategy was obtained by a Pd(0)-catalyzed decarboxylative allylation of a 2-arylcyclohexan-1-one-derived allylenol carbonate (87%, 96% ee).

Key words

Amaryllidaceae alkaloids - asymmetric total synthesis - oxomaritidine - dihydromaritidine - maritidine - epi-maritidine

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Referenzen

References and Notes
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