Seven-Step Stereodivergent Total Syntheses of Punicafolin and Macaranganin

Autor:	Takashi Tanaka, Takeo Kawabata, Hiromitsu Shibayama, Yoshihiro Ueda
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Colloid and Surface Chemistry Chemistry Stereochemistry Glycoside General Chemistry 010402 general chemistry Punicafolin 01 natural sciences Biochemistry Catalysis 0104 chemical sciences
Zdroj:	Journal of the American Chemical Society. 143:1428-1434
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.0c10714
Popis:	The first total syntheses of punicafolin (1) and macaranganin (2) were achieved in seven steps, respectively, from commercial α-d-glucose. The characteristic features of the synthesis are (1) sequential site-selective introduction of the adequate galloyl groups into unprotected d-glucose by a catalyst-controlled manner and (2) stereodivergent construction of the 3,6-HHDP bridge by oxidative phenol coupling of a common intermediate via a ring-flipping process of the glucose core. Because no protective groups were used for glucose throughout the process, extremely short-step total syntheses of natural glycosides 1 and 2 (MW 938) were performed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7c88f3a4651e04f9b809d45306de8b94 https://doi.org/10.1021/jacs.0c10714 Zobrazit plný text záznamu