Synthesis of the C5-C30 fragment of cyclodidemniserinol trisulfate via I2-mediated deprotection and ring closure tandem reaction

The Marine natural product cyclodidemniserinol trisulfate displayed moderate HIV-I integrase Inhibitory activity Irs novel structure triggered Out interest to synthesize it In our total synthesis effort, the natural product was dissected into four fragments based oil the rational retrosynthetic analysis All four fragments were successfully prepared with orthogonal protection And lie assembly of fragment A and B furnished the C-5-C-30 key subunit by employing the I-2-mediated deprotection intramolecular ketal formation tandem reaction in the presence of NaHO3 in MeCN Our work provided flexible and practical approaches to synthesize and derive the 3,5,7-trisubstituted 6,8-dioxabicyclo [3 2 1] octane based analogs to search for new structure HIV-I integrase inhibitors (C) 2009 Elsevier Lid All rights reserved