Total Syntheses of Urgineanins A, B, D, and Their Analogues
Received: 10 September 2016
Accepted after revision: 01 November 2016
28 November 2016 (online)
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.
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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: