Seven-Step Stereodivergent Total Syntheses of Punicafolin and Macaranganin

• DOI: 10.1021/jacs.0c10714
• Publication Date: 2021-01-15T04:59:49Z
• Authors: Hiromitsu Shibayama; Yoshihiro Ueda; Takashi Tanaka; Takeo Kawabata
• Keywords: 01 natural sciences; 0104 chemical sciences

The first total syntheses of punicafolin (1) and macaranganin (2) were achieved in seven steps, respectively, from commercial α-d-glucose. characteristic features the synthesis are sequential site-selective introduction adequate galloyl groups into unprotected d-glucose by a catalyst-controlled manner stereodivergent construction 3,6-HHDP bridge oxidative phenol coupling common intermediate via ring-flipping process glucose core. Because no protective used for throughout process, extremely short-step natural glycosides 1 2 (MW 938) performed.