Diastereodivergent and Regiodivergent Total Synthesis of Princepin and Isoprincepin in Both (7″ R,8″ R) and (7″ S,8″ S) Isomers

Manami Kobayashi; Hiroya Ueno; Naoto Yoshida; Hitoshi Ouchi; Tomohiro Asakawa; Fumihiko Yoshimura; Makoto Inai; Toshiyuki Kan

doi:10.1021/acs.joc.9b01965

Diastereodivergent and Regiodivergent Total Synthesis of Princepin and Isoprincepin in Both (7″ R,8″ R) and (7″ S,8″ S) Isomers

J Org Chem. 2019 Nov 1;84(21):14227-14240. doi: 10.1021/acs.joc.9b01965. Epub 2019 Oct 1.

Authors

Manami Kobayashi¹, Hiroya Ueno¹, Naoto Yoshida¹, Hitoshi Ouchi¹, Tomohiro Asakawa², Fumihiko Yoshimura¹, Makoto Inai¹, Toshiyuki Kan¹

Affiliations

¹ School of Pharmaceutical Sciences , University of Shizuoka , 52-1 Yada , Suruga-ku , Shizuoka 422-8526 , Japan.
² Tokai University Institute of Innovative Science and Technology , 4-1-1, Kitakaname , Hiratsuka-city , Kanagawa 259-1292 , Japan.

PMID: 31542931
DOI: 10.1021/acs.joc.9b01965

Abstract

The first total synthesis of (7″R,8″R)-, (7″S,8″S)-isomers of princepin (1) and (7″R,8″R)-, (7″S,8″S)-isomers of isoprincepin (2) was accomplished in a highly stereoselective manner via para quinomethide-mediated construction of the furofuran and 1,4-benzodioxane rings. Structural confirmation methods of 1 and 2 were established by CD and HPLC analysis of each diastereomers with natural products.

Publication types

Research Support, Non-U.S. Gov't