Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

Xin-Ting Hu; Qing-Yan Cheng; Yan-Ping Chen; Kun Li; Cai-Xian Yan; Dashan Li; Li-Dong Shao

doi:10.1007/s13659-024-00450-2

Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

Nat Prod Bioprospect. 2024 May 14;14(1):29. doi: 10.1007/s13659-024-00450-2.

Authors

Xin-Ting Hu^#¹, Qing-Yan Cheng^#¹, Yan-Ping Chen¹, Kun Li¹, Cai-Xian Yan², Dashan Li¹, Li-Dong Shao³

Affiliations

¹ Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650500, China.
² Yunnan Precious Metals Laboratory, Kunming Institute of Precious Metals, Kunming, 650106, China.
³ Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650500, China. shaolidong@ynucm.edu.cn.

^# Contributed equally.

Abstract

A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes 7 in 14-88% yields. Take advantage of the synthetic intermediate 7h, the key B/C rings in brazilin core could be constructed by the sequential of Friedel-Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel-Crafts reactions.

Keywords: 1,3-Diarylpropene; Brazilin; Catalytic Prins reaction; Hydroxymethylation/hydroxylation.

Abstract

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