Synthesis of the A/D/E-ring Core Compounds of Maoecrystal V

Hiroki Asao; Yasuharu Shimasaki; Ayaka Sasaki; Shunki Katayama; Kousuke Ida; Masaaki Kotake; Eriko Sato; Yuki Sato; Taiki Ishimoto; Minoru Izumi; Christopher J Vavricka; Kuwahara Shigefumi; Hiromasa Kiyota

doi:10.1093/bbb/zbae049

Synthesis of the A/D/E-ring Core Compounds of Maoecrystal V

Biosci Biotechnol Biochem. 2024 Apr 23:zbae049. doi: 10.1093/bbb/zbae049. Online ahead of print.

Authors

Affiliations

¹ Graduate School of Agricultural Science, Tohoku University, 468-1 Aramaki-aza-Aoba, Aoba, Sendai, Japan.
² Laboratory of Applied Natural Product Chemistry, Course of Agricultural Bioscience, Okayama University, 1-1-1 Tsushima-Naka, Kita, Okayama, Japan.
³ Department of Biotechnology and Life Science, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo, Japan.

PMID: 38653727
DOI: 10.1093/bbb/zbae049

Abstract

Synthesis of the A/D/E-ring core compounds of maoecrystal V was achieved. The key Diels-Alder reactions between tricyclic α-methylene lactones and Kitahara-Danishefsky dienes afforded the spirocyclic core compounds in a regioselective and stereoselective manner.

Keywords: Diels-Alder reaction; intramolecular aldol reaction; maoecrystal V; synthesis.