TY - JOUR

T1 - Biogenetic space-guided synthesis of rearranged terpenoids

AU - Alekseychuk, Mykhaylo

AU - Heretsch, Philipp

N1 - 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.

PY - 2023/5/10

Y1 - 2023/5/10

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85159308633&partnerID=8YFLogxK

U2 - 10.1039/d3cc01009k

DO - 10.1039/d3cc01009k

M3 - Article

C2 - 37162324

AN - SCOPUS:85159308633

VL - 59

SP - 6811

EP - 6826

JO - Chemical communications

JF - Chemical communications

SN - 1359-7345

IS - 45

ER -