514-62-5Relevant articles and documents
Synthesis of (-)-Chamobtusin A from (+)-Dehydroabietylamine
Mori, Naoki,Kuzuya, Kazuma,Watanabe, Hidenori
, p. 11866 - 11870 (2016)
Chamobtusin A, a unique diterpene alkaloid isolated from Chamaecyparis obtusa cv. tetragon, is considered to be biosynthesized from an abietane diterpenoid. On the basis of this biosynthetic hypothesis, ferruginol (15) was synthesized from (+)-dehydroabietylamine and then biomimetically transformed into (a?)-chamobtusin A in 6 steps (12 steps from (+)-dehydroabietylamine).
Brandt,Neubauer
, p. 683,685 (1940)
Briggs,Cambie
, p. 356 (1960)
Bispericyclic Diels–Alder Dimerization of ortho-Quinols in Natural Product (Bio)Synthesis: Bioinspired Chemical 6-Step Synthesis of (+)-Maytenone
Peixoto, Philippe A.,El Assal, Mourad,Chataigner, Isabelle,Castet, Frédéric,Cornu, Ana?lle,Coffinier, Romain,Bosset, Cyril,Deffieux, Denis,Pouységu, Laurent,Quideau, Stéphane
, p. 14967 - 14974 (2021)
Many natural products of plant or microbial origins are derived from enzymatic dearomative oxygenation of 2-alkylphenolic precursors into 6-alkyl-6-hydroxycyclohexa-2,4-dienones. These so-called ortho-quinols cyclodimerize via a remarkably selective bispericyclic Diels–Alder reaction. Whether or not the intervention of catalytic or dirigent proteins is involved during this final step of the biosynthesis of these natural products, this cyclodimerization of ortho-quinols can be chemically reproduced in the laboratory with the same strict level of site-specific regioselectivity and stereoselectivity. This unique yet unified process, which finds its rationale in the inherent chemical reactivity of those ortho-quinols, is illustrated herein by an efficient and bioinspired first chemical synthesis of one of the most structurally complex and synthetically challenging examples of such natural cyclodimers, the bisditerpenoid (+)-maytenone.
(+/-)-ferruginol analogs and preparation method thereof, and applications of (+/-)-ferruginol analogs in preparation of antibacterial drugs
-
, (2018/11/03)
The present invention discloses (+/-)-ferruginol analogs represented by formulas (I) and (II), and a preparation method thereof, wherein a tricyclic diterpene analog (1) is used as a raw material, andesterification, acylation, oxidation, reduction, dehydroxylation, deprotection, dehydration, halogenation, demethylation and other reactions are performed to obtain the (+/-)-ferruginol analogs represented by the formulas (I) and (II). The invention further discloses a total synthesis method of (+/-)-ferruginol, wherein a compound (16b) as a raw material and a Grignard reagent are subjected to aGrignard reaction, and a dehydroxylation reaction and a demethylation reaction are performed to obtain the (+/-)-ferruginol. According to the present invention, the prepared (+/-)-ferruginol analogs represented by the formulas (I) and (II) have significant antibacterial activity and can be potentially used for the preparation of antibacterial drugs. The formulas (I) and (II) are defined in the specification.
Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes
Tao, Zhonglin,Robb, Kevin A.,Zhao, Kuo,Denmark, Scott E.
supporting information, p. 3569 - 3573 (2018/03/21)
A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.
