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Synthesis 2017; 49(07): 1531-1537
DOI: 10.1055/s-0036-1588105
DOI: 10.1055/s-0036-1588105
paper
Total Syntheses of Urgineanins A, B, D, and Their Analogues
Further Information
Publication History
Received: 10 September 2016
Accepted after revision: 01 November 2016
Publication Date:
28 November 2016 (online)
Abstract
The first asymmetric total syntheses of urgineanins A, B, and D – potent antiproliferative homoisoflavonoids – were achieved by utilizing Pd-catalyzed allylic substitution of the allylic acetate with arylboronic acids for introduction of the C rings of homoisoflavonoid skeleton. Several unnatural urgineanin analogues were also prepared in this manner.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588105. 1H and 13C NMR spectra of 3–11, synthetic urgineanins A, B, D, and chiral chromatographic data of (+)-8a, (–)-8a, (+)-8b, (+)-8c, (+)-8d, (+)-8e, (+)-8f are included.
- Supporting Information
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References
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- 11 The ers of 8a and 8b were determined by chiral HPLC analysis (CHIRALPAK IA column; flow, 0.5 mL min–1; H2O–MeCN = 50:50; λ = 254 nm). See Supporting Infromation for details.
- 12 The er of 8e was determined by chiral HPLC analysis (CHIRALPAK IA column; flow, 0.5 mL min–1; H2O–MeCN = 50:50; λ = 254 nm). The ers of 8c and 8d were determined by chiral HPLC analysis (CHIRALPAK IC column; flow, 1 mL min–1; hexane–EtOH = 80:20; λ = 210 nm). The er of 8f was determined by chiral HPLC analysis (CHIRALPAK IA column; flow, 0.5 mL min–1; H2O–MeCN = 60:40; λ = 254 nm). See Supporting Information for details.
For reviews, see:
For reviews on IBX, see:
For the oxidation of alcohols with IBX in EtOAc, see: