First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP

Chaolei Wang, Guoxiang Wei, Xue Yang, Hequan Yao, Jieyun Jiang, Jie Liu, Mingqin Shen, Xiaoming Wu, Jinyi Xu

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The first asymmetric total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP has been achieved in 8 steps starting from commercially available 6-bromo-2-hydroxy-3-methoxybenzaldehyde. Key steps included intramolecular Heck reaction and oxidative ozonolysis reaction with the retention of stereochemistry. A latent functionality strategy was implemented to circumvent the racemization in this endeavor. The protocol described here provided a fast and easily accessible synthetic method to obtain optically pure isochroman-4-one derivatives. Furthermore, the in vivo antihypertensive effects of (±)-XJP, S-(+)-XJP and R-(-)-XJP were investigated on spontaneously hypertensive rats. The obtained results could provide valuable information to identify a promising lead for further chemical modification research. This journal is

Original languageEnglish
Pages (from-to)7338-7344
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number37
DOIs
StatePublished - Oct 7 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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