Concise synthesis of the bioactive natural polyhydroxynaphthoate parvinaphthol B via Hauser-Kraus annulation. Issue 51 (20th December 2017)

• Record Type: Journal Article
• Authors: Ahn, Sungwan; Han, Young Taek
• Is Part Of: Tetrahedron letters. Volume 58:Issue 51(2017)
• Page Start: 4779
• Page End: 4780
• Publication Date: 2017-12-20
• Subjects: Parvinaphthol B -- Hauser-Kraus annulation -- Polyhydroxynaphthoate -- Total synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.11.024
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The first synthesis of the parvinaphthol B was presented. The efficient synthetic route toward polyhydroxynaphthoate skeleton was described. The selective ether-bond cleavage was also investigated. Abstract: Herein, we describe the first total synthesis of parvinaphthol B, a polyhydroxynaphthoate derived from the root of Pentas parvifolia which exhibits cytotoxic effects against the TNBC cell line. The key feature of the synthesis involves a Hauser-Kraus annulation to provide the polyhydroxynaphthoate skeleton. The synthesis requires only six linear steps and afforded the product in 26.5% overall yield, thus representing a simple method for the further preparation of analogs and biological studies.