Collective Total Synthesis of β-Carboline-Type Monoterpenoid Indole Alkaloid Glycosides

Sakamoto, Jukiya; Hiruma, Daiki; Kitajima, Mariko; Ishikawa, Hayato

doi:10.1055/a-2053-1629

Cited by 5 publications

(2 citation statements)

References 29 publications

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“…We have recently achieved a collective total synthesis of monoterpenoid indole alkaloids along a biosynthetic tree diagram. [13][14][15][16][17][18][19][20][21] In this study, we conceived an alternative biosynthetic hypothesis for 1 (Chart 2). Our proposed biosynthesis begins with a connection by the reductive amination of tryptamine and secologanin (2).…”

Section: Introductionmentioning

confidence: 99%

Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

Imaoka,

Nakashima,

Kitajima

et al. 2024

CHEMICAL & PHARMACEUTICAL BULLETIN

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The first enantioselective total synthesis of kopsiyunnanine B, which has a unique folded and complex pentacyclic structure containing six contiguous chiral centers, has been achieved along our originally proposed biosynthetic pathway. The key reaction of this synthesis includes a bioinspired cascade that builds three ring structures and three chiral centers in one step and features the stereoselective reduction of a β-acrylate and oxidation to an oxindole.

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Section: Introductionmentioning

confidence: 99%

Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

Imaoka,

Nakashima,

Kitajima

et al. 2024

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…4 Ishikawa and co-workers achieved the collective and efficient asymmetric total syntheses of five -carboline-type monoterpenoid indole alkaloid glycosides, employing a series of bioinspired reactions developed to provide different alkaloid skeletons. 5 Practical and scalable enantioselective total syntheses of the marine anticancer sesquiterpene quinone meroterpenoids (+)-dysidavarones A-C have been accomplished by Lu and co-workers. 6 Furthermore, She, Li and co-workers have summarized the recent progress on the biomimetic synthesis of gymnotheligans based on their plausible biogenetic pathway proposal.…”

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confidence: 99%

Cluster Preface: Biomimetic Synthesis

Deng,

Tang

2024

Synlett

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Jun Deng (left) received his B.Sc. from Lanzhou University and his Ph.D. from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (2014) with Professor Ang Li. After a short period of postdoctoral research in the lab of Professor Andrew Myers at Harvard University (2014–2016), he was appointed a Pioneer ‘Hundred Talents Program’ Researcher at Kunming Institute of Botany, Chinese Academy of Sciences in 2017. In December 2020, he moved to Nankai University where he is a professor at the College of Chemistry. He received the Thieme Journals Award (2020). His research focuses on natural product total synthesis and medicinal chemistry. Yefeng Tang (right) earned his B.S. from Lanzhou University (1995–1999) and his M.S. from the Institute of Materia Medica, Chinese Academy of Medical Science (1999–2002). From 2003 to 2006, he pursued his Ph.D. under the guidance of Professor Zhen Yang and Professor Jiahua Chen at Peking University. Subsequently, he conducted postdoctoral research with Prof. K. C. Nicolaou at The Scripps Research Institute between 2006 and 2009. In 2010, he commenced his independent career at the School of Pharmaceutical Sciences, Tsinghua University, where he is now a tenured professor. His primary research interests encompass the total synthesis of natural products, the development of synthetic methodologies, and the discovery of antiviral and anti-aging drugs.

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Bioinspired Total Syntheses of Secologanin-Related Natural Products: A Demonstration of the Power of Secologanin in the Flask

Sakamoto¹,

Ishikawa²

2023

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The biosynthetic pathways of most natural products branch out like a tree diagram. Secologanin is one of the intermediates that can be considered a vertex in such a diagram. In this account, our first asymmetric total synthesis of secologanin and the collective total synthesis of monoterpenoid indole alkaloids and hetero-oligomeric iridoid glycosides utilizing the versatility of secologanin are reported.

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Collective Total Synthesis of β-Carboline-Type Monoterpenoid Indole Alkaloid Glycosides

Cited by 5 publications

References 29 publications

Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

Cluster Preface: Biomimetic Synthesis

Bioinspired Total Syntheses of Secologanin-Related Natural Products: A Demonstration of the Power of Secologanin in the Flask

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