Collective Total Synthesis of Secologanin-Related Natural Products-Reference-Cited by-同舟云学术

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Collective Total Synthesis of Secologanin-Related Natural Products

Published:2024 Issue: Volume: Page:181-204
ISSN:
Container-title:Modern Natural Product Synthesis
language:en
Short-container-title:

Author:

Sakamoto Jukiya,Ishikawa Hayato

Abstract

AbstractWe have been interested in the reactivity of secologanin, which is transformed into more than 3000 natural products in nature and have been working on the bioinspired synthesis of several natural products using secologanin derivatives. In this chapter, we describe the total synthesis of secologanin using an organocatalytic reaction and the collective and divergent total synthesis of glycosylated monoterpenoid indole alkaloids and hetero-oligomeric iridoid glycosides through biogenetically inspired transformations from secologanin derivatives.

Publisher

Springer Nature Singapore

Link

https://link.springer.com/content/pdf/10.1007/978-981-97-1619-7_9

Reference29 articles.

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2. Baran PS (2018) Natural Product Total Synthesis: As Exciting as Ever and Here To Stay. Journal of the American Chemical Society 140: 4751–4755. https://doi.org/10.1021/jacs.8b02266

3. Li L, Chen Z, Zhang X, Jia Y (2018) Divergent Strategy in Natural Product Total Synthesis. Chemical Reviews 118: 3752–3832. https://doi.org/10.1021/acs.chemrev.7b00653

4. Poupon E, Nay B (eds) (2011) Biomimetic Organic Synthesis. Wiley, Weinheim, https://doi.org/10.1002/9783527634606

5. a) Rakumitsu K, Sakamoto J, Ishikawa H (2019) Total Syntheses of (−)-Secologanin, (−)-5-Carboxystrictosidine, and (−)-Rubenine. Chemistry A European Journal 25: 8996–9000. https://doi.org/10.1002/chem.201902073; b) Sakamoto J, Umeda Y, Rakumitsu K, Sumimoto M, Ishikawa H (2020) Total Syntheses of (−)-Strictosidine and Related Indole Alkaloid Glycosides. Angewandte Chemie International Edition 59: 13414–13422. https://doi.org/10.1002/anie.202005748; Angewandte Chemie 132: 13516–13524. https://doi.org/10.1002/ange.202005748; c) Sakamoto J, Ishikawa H (2021) Bioinspired Transformations Using Strictosidine Aglycones: Divergent Total Syntheses of Monoterpenoid Indole Alkaloids in the Early Stage of Biosynthesis. Chemistry A European Journal 28: e202104052. https://doi.org/10.1002/chem.202104052; d) Nakashima N, Sakamoto J, Rakumitsu K, Kitajima M, Juliawaty LD, Ishikawa H (2022) Secorubenine, a Monoterpenoid Indole Alkaloid Glycoside from Adina rubescens: Isolation, Structure Elucidation, and Enantioselective Total Synthesis. Chemical and Pharmaceutical Bulletin 70: 187–191. https://doi.org/10.1248/cpb.c21-00931; e) Sakamoto J, Kitajima M, Ishikawa H (2022) Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine. Chemical and Pharmaceutical Bulletin 70: 662–668. https://doi.org/10.1248/cpb.c22-00441; f) Yoshidome A, Sakamoto J, Kohara M, Shiomi S, Hokaguchi M, Hitora Y, Kitajima M, Tsukamoto S, Ishikawa H (2023) Divergent Total Syntheses of Hetero-Oligomeric Iridoid Glycosides. Organic Letters 25: 347–352. https://doi.org/10.1021/acs.orglett.2c03965; g) Sakamoto J, Kitajima M, Ishikawa H (2023) Total Syntheses of (+)-Villocarine A, (−)-Apogeissoschizine, and (+)-Geissoschizine. Chemistry A European Journal 29: e202300179. https://doi.org/10.1002/chem.202300179; h) Sakamoto J, Hiruma D, Kitajima M, Ishikawa H (2024) Collective Total Synthesis of β-Carboline-Type Monoterpenoid Indole Alkaloid Glycosides. Synlett 35: 576–581. https://doi.org/10.1055/a-2053-1629; review see; i) Sakamoto J, Ishikawa H (2023) Bioinspired Total Syntheses of Secologanin-Related Natural Products: A Demonstration of the Power of Secologanin in the Flask. Synlett. https://doi.org/10.1055/a-2079-7989; j) Ishikawa H (2023) Collective Synthesis of Monoterpenoid Indole Alkaloids Using Bioinspired Strategies. In: Ishikawa H, Takayama H (eds) New Tide of Natural Product Chemistry. Springer, Singapore, p 211–234, https://doi.org/10.1007/978-981-99-1714-3.

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