title: Synthesis of a key intermediate, 10-acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol, in the synthesis of pseudolaric acid A.
abstract: 10-Acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol was synthesized by aldol cyclization to a five-membered ring, epoxidation, samarium diiodide-induced ring opening, and the RCM reaction to the seven-membered carbocycle. This method has succeeded in constructing the desired stereochemistry in the synthesis of pseudolaric acid A.
authors: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors: Katsuyuki
authors: K
authors: Nakashima
authors: Naoki
authors: N
authors: Kikuchi
authors: Tasuku
authors: T
authors: Takehara
authors: Takayuki
authors: T
authors: Shiozawa
authors: Shigeru
authors: S
authors: Takaoka
authors: Motoo
authors: M
authors: Tori
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D012493:Samarium / Q000737:chemistry; D012833:Siloxanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C583576:10-acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo(5.3.0)dec-4-en-1-ol; D001643:Bridged Bicyclo Compounds; D004224:Diterpenes; D007454:Iodides; D012833:Siloxanes; D012493:Samarium; C058390:pseudolaric acid A; C409809:samarium diiodide