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, Table of Contents

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

Authors

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

Abstract

All articles of this category

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

Full Text

References

References and Notes
1 Jin Z, Yao G. Nat. Prod. Rep. 2019; 36: 1462 ; and references cited therein
2 Ding Y, Qu D, Zhang K.-M, Cang X.-X, Kou Z.-N, Xiao W, Zhu J.-B. J. Asian Nat. Prod. Res. 2016; 19: 53

3a Refaat J, Kamel MS, Ramadan MA, Ali AA. Int. J. Pharm. Sci. Res. 2013; 4: 1239
3b Jin Z. Nat. Prod. Rep. 2016; 33: 1318

4a Zhang Y, Shen S, Fang H, Xu T. Org. Lett. 2020; 22: 1244
4b Williams P, Sorribas A, Howes M.-JR. Nat. Prod. Rep. 2011; 28: 48 ; and references cited therein

5a Zhang Y, Shen S, Fang H, Xu T. Org. Lett. 2020; 22: 1244
5b Kogure N, Katsuta N, Kitajima M, Takayama H. Chem. Pharm. Bull. 2011; 59: 1545

6a Bru C, Thal C, Guillou C. Org. Lett. 2003; 5: 1845
6b Roe C, Stephenson GR. Org. Lett. 2008; 10: 189
6c Pandey G, Gupta NR, Pimpalpalle TM. Org. Lett. 2009; 11: 2547 ; and references cited therein

7a Wang W, Dai J, Yang Q, Deng Y.-H, Peng F, Sao Z. Org. Lett. 2021; 23: 920 ; and references cited therein
7b Verma P, Chandra A, Pandey G. J. Org. Chem. 2018; 83: 9968

8a Tomioka K, Koga K, Yamada S. Chem. Pharm. Bull. 1977; 25: 2681
8b Zuo X.-D, Guo S.-M, Yang R, Xie J.-H, Zhou Q.-L. Chem. Sci. 2017; 8: 6202

9a Boit H. -G. Chem. Ber. 1956; 89: 1129
9b Feinstein AI, Wildman WC. J. Org. Chem. 1976; 41: 2447

10a Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Christoffers J, Baro A. Wiley-VCH; Weinheim: 2005
10b Das JP, Marek I. Chem. Commun. 2011; 47: 4593

11a Trost BM, Fandrick DR. Aldrichimica Acta 2007; 40: 59
11b Behenna DC, Stoltz BM. J. Am. Chem. Soc. 2004; 126: 15044
11c Ghosh S, Chaudhuri S, Bisai A. Chem. Eur. J. 2015; 21: 17479

12a Trost BM, Schroeder GM, Kristensen J. Angew. Chem. Int. Ed. 2002; 41: 3492
12b Trost BM, Xu J, Schmidt T. J. Am. Chem. Soc. 2009; 131: 18343
12c Park J, Kim YK, Kim G. Bull. Korean Chem. Soc. 2011; 32: 3141

13 Pupo G, Properzi R, List B. Angew. Chem. Int. Ed. 2016; 55: 6099
14 Das MK, Kumar N, Bisai A. Org. Lett. 2018; 20: 4421

For the use of [3,3]-sigmatropic rearrangements in total syntheses of Amaryllidaceae alkaloids from our group, see:

15a Das MK, De S, Subhashish S, Bisai A. Org. Biomol. Chem. 2015; 13: 3585
15b Majumder S, Yadav A, Pal S, Khatua A, Bisai A. J. Org. Chem. 2022; 87: 7786

16a Ito Y, Hirao T, Saegusa T. J. Org. Chem. 1978; 43: 1011
16b Bisai A, West SP, Sarpong R. J. Am. Chem. Soc. 2008; 130: 7222

17 The relative stereochemistry of epoxyketone (–)-14 was assigned by analogy with a report in the literature; see ref. 14.
18 Energy minimization of (–)-deoxymaritidine (24) was performed by an MM2 calculation; ChemBio3D Ultra 14. PerkinElmer Informatics; Waltham (MA, USA): 2022

Supplementary Material

Supporting Information (PDF)