title: Total synthesis, structural elucidation, and structure-cytotoxic activity relationship of (-)-gummiferol.
abstract: A highly stereoselective and stereodivergent synthesis of two possible diastereomers of (-)-gummiferol was achieved, wherein the stepwise epoxidation and Cadiot-Chodkiewicz reaction were utilized for the construction of the diepoxide moiety and triacetylene part, respectively. Detailed comparison of their (1)H and (13)C NMR data and specific rotation with those of the natural product unambiguously elucidated the absolute stereostructure of gummiferol. In addition, the cytotoxic activity of the synthesized gummiferol, its stereoisomers, and its truncated analogues was evaluated, which clearly indicates that (1) the absolute configuration of the diepoxide moiety has little influence on the cytotoxic activity against human cancer cells and (2) the triacetylene unit is the crucial structural element required for exerting the cytotoxic activity.
authors: Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan. takamura@cc.okayama-u.ac.jp
authors: Hiroyoshi
authors: H
authors: Takamura
authors: Hiroko
authors: H
authors: Wada
authors: Nan
authors: N
authors: Lu
authors: Osamu
authors: O
authors: Ohno
authors: Kiyotake
authors: K
authors: Suenaga
authors: Isao
authors: I
authors: Kadota
mesh_terms: D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000085:Acetates; D000972:Antineoplastic Agents, Phytogenic; D005233:Fatty Alcohols; C097940:gummiferol