- Synthesis of moracin C and its derivatives with a 2-arylbenzofuran motif and evaluation of their PCSK9 inhibitory effects in HepG2 cells
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Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a key factor in several cardiovascular diseases, as it is responsible for the elevation of circulating low-density lipoprotein cholesterol (LDL-C) levels in blood plasma by direct interaction with t
- BasavanaGowda, Melanayakanakatte Kuberappa,Chae, Hee-Sung,Choi, Won Jun,Masagalli, Jagadeesh Nagarajappa
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- Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus
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In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential.
- Wu, Deyan,Mei, Hanbing,Tan, Ping,Lu, Weiqiang,Zhu, Jin,Wang, Wei,Huang, Jin,Li, Jian
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p. 4383 - 4387
(2015/06/22)
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- Total synthesis of moracin C
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Moracin C has been synthesised by the most efficient route to date (10 steps and 12% overall yield). The relatively unexplored acid-induced, intramolecular migration of an acyl group from an ortho phenolic hydroxy to a benzylic hydroxy is used to synthesise o-hydroxybenzylphosphonium salts containing ester groups. The phosphonium salts are coupled with 3,5-dimethoxybenzoic acid. Intramolecular Wittig reaction then gives 2-arylbenzo[b]furans, bearing the key 1′,3′,5′ substitution pattern on the aryl ring. This discovery provides a concise route to polyphenolic benzo[b]furans that we expect to be of general utility.
- McAllister, Graeme D.,Hartley, Richard C.,Dawson, Michael J.,Knaggs, Andrew R.
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p. 3453 - 3457
(2007/10/03)
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- Oviposition Stimulants for the Lesser Mulberry Pyralid, Glyphodes pyloalis (WALKER), in Mulberry Leaves; Rediscovery of Phytoalexin Components as Insect Kairomones
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The oviposition stimulant for the lesser mulberry pyralid, Glyphodes pyloalis WALKER, was isolated from an acetone extract of mulberry (Morus alba L.) leaves, and its structure was identified as 2-(3',5'-dihydroxy-4'-prenylphenyl)-6-hydroxybenzofuran, viz
- Matsuyama, Shigeru,Kuwahara, Yasumasa,Nakamura, Shigeko,Suzuki, Takahisa
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p. 1333 - 1341
(2007/10/02)
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