Diversity oriented synthesis of hispanane-like terpene derivatives from (R)-(+)-sclareolide.
(R)-(+)-Sclareolide 1 has been used as a starting material to develop a diversity oriented methodology to access hispanane 28 a, and hispanane-like derivatives 27 b-27 e. This methodology is based on the intramolecular Friedel-Crafts acylation of the corresponding 12-desoxylabdanoic-like acids 27, for the construction of the cycloheptane ring which is characteristic of the hispananes. Acids 27 are obtained from alcohols 20, available by addition of the lithium or magnesium reagents to amide 12 (followed by Luche reduction), or to aldehyde 21. This sequence has resulted in the preparation of hispanane framework 27 a. The versatility of this methodology therefore allows a structural diversity oriented synthesis, since it allows the access to a wide variety of hispanane-like derivatives.
de la Torre
María C
MC
Instituto de Química Orgánica, Dpto. de Productos Naturales, CSIC, Madrid, Spain. iqot310@iqog.csic.es
García
Isabel
I
Sierra
Miguel A
MA
D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D004224:Diterpenes; D013729:Terpenes; C506867:hispanane; C109395:sclareolide