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Total Synthesis of Avrainvillamide (CJ-17,665) and Stephacidin B

✍ Scribed by Phil S. Baran; Carlos A. Guerrero; Benjamin D. Hafensteiner; Narendra B. Ambhaikar

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 318 KB
Volume: 44
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.200500655

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Scheme 3. Synthesis of simple avrainvillamide model 15 and the successful conversion of (+)-1 into (+)-3 and (À)-2. Reagents and conditions: a) NaBH 3 CN (10 equiv), AcOH, 25 8C, 12 h, 53 %; b) Na 2 WO 4 •2 H 2 O (0.2 equiv), aq. 35 % H 2 O 2 (50 equiv), MeOH, H 2 O, 25 8C, 6 h, ca. 30 %; c) NaBH 3

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