Synthesis of the furo[2,3-b]chromene ring system of hyperaspindols A and B

• Danielle L. Paterson and
• David Barker

Beilstein J. Org. Chem. 2015, 11, 265–270, doi:10.3762/bjoc.11.29

• Danielle L. Paterson David Barker School of Chemical Sciences, University of Auckland, 23 Symonds St, Auckland, New Zealand 10.3762/bjoc.11.29 Abstract The synthesis of the unique furo[2,3-b]chromene ring system found in hyperaspidinols A and B, acylphloroglucinols from Hypericum chinense has

• been achieved in twelve steps. By comparison of the NMR spectra of the synthesized compounds with those of the natural products, a relative stereochemistry is suggested, especially that of the ketal carbon. Keywords: acylphloroglucinols; bicyclisation; furo[2,3-b]chromene; fused ketal; Introduction

• been isolated from H. chinense including prenylated acylphloroglucinols such as chinesins I (3) and II (4), xanthones, flavonoids, terpenoids, naphthodianthrones, and norlignans, such as hyperione A (5) and B (6) [1][6][7][8]. Chinesins I (3) and II (4) are acylphloroglucinol derivatives which possess

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• , acylphloroglucinols, quinolone-substituted phenols and 4-amino-2-sulfanylphenol derivatives are discussed. Some important aspects of the described pharmacological activities of the compounds are summarized in Table 3. Review 4-Hydroxybenzyl alcohol 4-Hydroxybenzyl alcohol (HBA, 1) (Figure 1) is a well-known phenolic

• , which were reacted without further purification with R2SH thiols. The addition to the unsaturated system yielded the target compound 28 with different arylthiol groups under rearomatization. Acylphloroglucinol derivatives Acylphloroglucinols are typical secondary metabolites biosynthetically derived

• drug candidate nor a good model compound. The finding that structurally simpler, natural, acylphloroglucinol derivatives also showed antiproliferative effects against endothelial cells with inhibitory effects in a tube-formation assay on Matrigel catalyzed the search for simple acylphloroglucinols with