Preparation of Ambrox from Labdanes of Dysoxylum hongkongense, and the Preparation of New Diterpenoids from Dysoxylum hongkongense

摘要

The present invention discloses eight new diterpenoids, i.e. Dysongensins A to H, extracted from the leaves and twigs of Dysoxylum hongkongense, wherein AMBROX® which is applicable in the perfume industry is prepared from Dysongensin A via a series of chemical reactions, and the cytotoxicity of Dysongensins A to H against human cancer cell lines and their antiviral and anti-inflammatory activities are determined. Therefore, in the present invention, AMBROX® prepared from Dysongensin A is a new idea for application as an odorous compound in the perfume industry, and the novel diterpenoids can be prepared as a pharmaceutical compositions and/or a drug having antiviral, anti-inflammatory and/or anti-cancer activities.

主权项

1. A method for preparing (−)-8,12-epoxy-13,19,15,16-tetranorlabdane, comprising steps of:
(a) providing a diterpenoid represented by formula (I): wherein the diterpenoid of formula (I) is extracted from a Dysoxylum hongkongense, (b) oxidatively transforming the diterpenoid of formula (I) to form a diterpenoid of formula (II): (c) reducing the diterpenoid of formula (II) with a sodium borohydride to form a 3-hydroxy-sclareolide; (d) reacting the 3-hydroxy-sclareolide with a methanesulfonyl chloride to form a 3-mesyloxy sclareolide; (e) reacting the 3-mesyloxy sclareolide with a lithium aluminium hydride followed by dehydrocyclization using a p-toluenesulfonic acid (TsOH.H2O) in a nitromethane to form a 3-mesyloxy ambrox; (f) reacting the 3-mesyloxy ambrox with a lithium chloride to form a Δ2(3)-ambrox; and (g) treating the Δ2(3)-ambrox with a hydrogen gas to form the (−)-8,12-epoxy-13,14,15,16-tetranorlabdane.