Total Synthesis of Cytotoxic Macrolide Amphidinolide B1 and the

Aug 12, 2008 - Genoveffa Nuzzo , Bruno A. Gomes , Elvira Luongo , Maria C. M. Torres , Evelyne A. Santos , Adele Cutignano , Otília D. L. Pessoa , Le...
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Total Synthesis of Cytotoxic Macrolide Amphidinolide B1 and the Proposed Structure of Amphidinolide B2 [J. Am. Chem. Soc. 2008, 130, 7253–7255]. Liang Lu, Wei Zhang, and Rich G. Carter*

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The ordering of conditions in Scheme 5 for the last two steps in the synthesis of compounds 2 and 30 was inadvertently switched. Both the text of the manuscript and the Supporting Information are presented in the correct order. The correct ordering for Scheme 5 is shown below. Scheme 5. Synthesis of Proposed Structure of Amphidinolide B2

and its C8,9 Diastereomera

a (i) (S)-CBS, BH3 · DMS, THF, -20 °C, 3 h, >10:1 dr, 67%; (ii) Ti(OiPr)4, TBHP, CH2Cl2, -20 °C, 5 h, mol sieves, 74%, 2:1 dr (24/25); (iii) Bu3P, o-NO2C6H4SeCN, THF; (iv) TAS-F, DMF/THF/H2O (10:1:0.02), 0 °C; (v) TMSOOTMS, NaHCO3, CH2Cl2.

JA8049518 10.1021/ja8049518 Published on Web 08/12/2008 11834

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J. AM. CHEM. SOC. 2008, 130, 11834–11834

10.1021/ja8049518 CCC: $40.75  2008 American Chemical Society