Sequential transesterifications dominated reversible conversion of phragmalin-type 8/9/11-and 8/9/30-orthoesters

Autor:	Yong Yin, Haohao Li, Wansha Huang, Jun Luo, Ling-Yi Kong, Sheng-Mou Hu
Rok vydání:	2021
Předmět:	Chemistry Stereochemistry Organic Chemistry Protonation Limonoid Biochemistry chemistry.chemical_compound Phragmalin Drug Discovery medicine Moiety Organic synthesis Orthoester medicine.drug
Zdroj:	Tetrahedron Letters. 81:153363
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2021.153363
Popis:	Orthoesters based on phragmalin-type limonoid from Meliaceae family is an important branch of plant orthoesters, and it is mainly existed as 1/8/9-, 8/9/11-, 8/9/14-, or 8/9/30-types. In the process of exploring the biogenetic pathway of the orthoester moiety in phragmalins, the reversible conversion between 8/9/11-orthoerter (tabularisin A, 1) and 8/9/30-orthoester (tabularisin C, 2) under acid-catalyzed condition were found and optimized. The protonated orthoester or ester group triggered sequential transesterifications may be the key steps of this reversible rearrangement. This research not only revealed a novel rearrangement mode involving multiple groups in organic synthesis, but also suggested the close biosynthetic relationship between 8/9/11- and 8/9/30-phragmalin-type orthoesters.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3c624dba69a90dd418deb3665a49bafb https://doi.org/10.1016/j.tetlet.2021.153363 Zobrazit plný text záznamu Full Text from ScienceDirect