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

Organic & Biomolecular Chemistry Pub Date: 2014-07-29 DOI: 10.1039/C4OB01470G

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.

Graphical abstract: First total synthesis of antihypertensive natural products S-(+)-XJP and R-(?)-XJP
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