Synthesis of racemic orobanchols via acid-mediated cascade cyclization: Insight into the process of BC-ring formation in strigolactone biosynthesis

Autor:	Hironori Okamura, Takatoshi Wakabayashi, Nanami Shiotani, Hirosato Takikawa, Yusuke Ogura, Yukihiro Sugimoto
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Electrocyclic reaction Stereochemistry Organic Chemistry Biochemistry chemistry.chemical_compound chemistry Biosynthesis Drug Discovery Moiety Conrotatory and disrotatory Lactone Derivative (chemistry) Function (biology) Butenolide
Zdroj:	Tetrahedron Letters. 85:153469
ISSN:	0040-4039
Popis:	Strigolactones, a class of apocarotenoids, are known to function as rhizosphere semiochemicals and plant hormones. Canonical strigolactones consist of a tricyclic lactone (ABC-rings) and a butenolide moiety (D-ring), and their biosynthesis has been extensively studied. However, the process of BC-ring formation is yet to be clarified. The conversion of an 18-oxocarlactonoate derivative into racemic orobanchols was performed in the same way as in our previous study, which demonstrated that the BC-ring formation is possible “in flask” via acid-mediated cascade cyclization. The results strongly suggested that the mechanism of acid-mediated BC-ring formation may be based on the conrotatory electrocyclic reaction, and may provide significant insights into the process of BC-ring formation in strigolactone biosynthesis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::12dd3212e8f87c00db814850da5fb478 https://doi.org/10.1016/j.tetlet.2021.153469 Zobrazit plný text záznamu Full Text from ScienceDirect