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Synlett 2023; 34(07): 858-862
DOI: 10.1055/a-1912-2378
DOI: 10.1055/a-1912-2378
cluster
Chemical Synthesis and Catalysis in India
Asymmetric Total Syntheses of (–)-Dihydromaritidine and (–)-Oxomaritidine
Financial 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.
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-maritidineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1912-2378.
- Supporting Information
Publication History
Received: 19 June 2022
Accepted after revision: 28 July 2022
Accepted Manuscript online:
28 July 2022
Article published online:
19 August 2022
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For the use of [3,3]-sigmatropic rearrangements in total syntheses of Amaryllidaceae alkaloids from our group, see: