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Synlett 2023; 34(07): 858-862
DOI: 10.1055/a-1912-2378
cluster
Chemical Synthesis and Catalysis in India

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

Abhinay Yadav‡
a   Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal–462 066, Madhya Pradesh, India
,
Satyajit Majumder‡
a   Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal–462 066, Madhya Pradesh, India
,
Mrinal Kanti Das
b   Department of Chemistry, Karimpur Pannadevi College, University of Kalyani, Nadia–741 152, West Bengal, India
,
Ayan Mondal
c   Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia–741 246, West Bengal, India
,
Alakesh Bisai∗
a   Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal–462 066, Madhya Pradesh, India
c   Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia–741 246, West Bengal, India
› Author AffiliationsFinancial support from the SERB, DST (CRG/2019/000113, and STR/2020/000066) and CSIR [02(0403)/21/EMR-II], Government of India, is gratefully acknowledged.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1912-2378.
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Publication History

Received: 19 June 2022

Accepted after revision: 28 July 2022

Accepted Manuscript online:
28 July 2022

Article published online:
19 August 2022

© 2022. Thieme. All rights reserved

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