Biogenetic space-guided synthesis of rearranged terpenoids

authored by: Mykhaylo Alekseychuk, Philipp Heretsch
Abstract: Natural product chemistry is constantly challenged by newly discovered, complex molecules. Elements of complexity arise from unprecedented frameworks, with a large amount of densely packed stereogenic centres and different functional groups along with a generally high oxidation state. As a prime example, rearranged triterpenoids possess all these elements. For their total synthesis, a limit of what is considered sensible in terms of steps and yield is frequently reached. As an alternative, semisynthetic approaches have gained a great amount of attention in recent years. In this featured article, we present our and others' contributions towards the development of efficient and economic syntheses of complex terpenoid natural products and elaborate on the underlying rationale of biogenetic space-guided synthetic analysis.
Organisation(s): Institute of Organic Chemistry
Type: Article
Journal: Chemical communications
Volume: 59
Pages: 6811-6826
No. of pages: 16
ISSN: 1359-7345
Publication date: 10.05.2023
Publication status: Published
Peer reviewed: Yes
ASJC Scopus subject areas: Electronic, Optical and Magnetic Materials, Catalysis, Ceramics and Composites, Chemistry(all), Surfaces, Coatings and Films, Metals and Alloys, Materials Chemistry
Electronic version(s): https://doi.org/10.1039/d3cc01009k (Access: Open)

BibTeX

@article{3c15f3acbf614499ae0d072c2c29ec4e,
title = "Biogenetic space-guided synthesis of rearranged terpenoids",
abstract = "Natural product chemistry is constantly challenged by newly discovered, complex molecules. Elements of complexity arise from unprecedented frameworks, with a large amount of densely packed stereogenic centres and different functional groups along with a generally high oxidation state. As a prime example, rearranged triterpenoids possess all these elements. For their total synthesis, a limit of what is considered sensible in terms of steps and yield is frequently reached. As an alternative, semisynthetic approaches have gained a great amount of attention in recent years. In this featured article, we present our and others' contributions towards the development of efficient and economic syntheses of complex terpenoid natural products and elaborate on the underlying rationale of biogenetic space-guided synthetic analysis.",
author = "Mykhaylo Alekseychuk and Philipp Heretsch",
note = "Funding Information: Financial support for this work was provided by the European Research Council (ERC Consolidator Grant “RadCrossSyn”), Deutsche Forschungsgemeinschaft (Heisenberg-Program HE 7133/8-1) and Boehringer Ingelheim Stiftung (plus3 perspectives program). We would like to thank our former and current group members who worked on the projects highlighted here (Sinan C. A. Adrian, Maximilian G. Bauer, Dr Fenja L. Duecker and Dr Robert C. Heinze). Finally, we would like to thank an unknown reviewer for his/her valuable comments.",
year = "2023",
month = may,
day = "10",
doi = "10.1039/d3cc01009k",
language = "English",
volume = "59",
pages = "6811--6826",
journal = "Chemical communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "45",
}