Efficient Asymmetric Synthesis of abeo-Abietane-Type Diterpenoids by Using the Intramolecular Heck Reaction

• Published in: Journal of organic chemistry Vol. 75; no. 1; pp. 190 - 196
• Main Authors: Node, Manabu, Ozeki, Minoru, Planas, Loïc, Nakano, Masashi, Takita, Hirofumi, Mori, Daisuke, Tamatani, Shinji, Kajimoto, Tetsuya
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.01.2010; Amer Chemical Soc
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Catalysis; Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Cyclization; Diterpenes - chemical synthesis; Diterpenes - chemistry; Diterpenes, Abietane - chemical synthesis; Diterpenes, Abietane - chemistry; Exact sciences and technology; Ligands; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Terpenoids; ROUTE; BARK; (+/-)-DICHROANONE; ARYLATION; AROMATASE; THUJA-STANDISHII; (+/-)-TAIWANIAQUINOL-B; Intramolecular reaction; Racemic; Terpenoid; Terpene; Asymmetric synthesis; Diterpene; Heck reaction; Enantiomeric excess; Aromatic compound; Chemical synthesis; Fluorene derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo901972b

The synthesis of the abeo-abietane-type diterpenoids, i.e., (−)-dichroanal B, (−)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).