title: Total synthesis of the proposed structure of didemnaketal B.
abstract: Total synthesis of the proposed structure of didemnaketal B has been accomplished. The C7-C21 spiroacetal domain was synthesized by exploiting our Suzuki-Miyaura coupling/spiroacetalization strategy. The C1-C7 acyclic domain was constructed via an Evans syn-aldol reaction and a vinylogous Mukaiyama aldol reaction. Finally, the C22-C28 side chain was introduced by means of a Nozaki-Hiyama-Kishi reaction. Comparison of the NMR spectroscopic data of our synthetic material with those of the authentic sample revealed that the proposed structure requires stereochemical reassignment.
authors.affiliation: Gradutate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Sendai 980-8577, Japan. hfuwa@m.tohoku.ac.jp
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
authors.forename: Kumiko
authors.initials: K
authors.lastname: Sekine
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013141:Spiro Compounds; D013729:Terpenes; C554891:didemnaketal B