39707-56-7Relevant articles and documents
Expediently Scalable Synthesis and Antifungal Exploration of (+)-Yahazunol and Related Meroterpenoids
Zhang, Shasha,Wang, Xia,Hao, Jin,Li, Dangdang,Csuk, René,Li, Shengkun
supporting information, p. 2010 - 2017 (2018/09/25)
The efficient synthesis and antifungal exploration of (+)-yahazunol and related natural products are described. Central to this strategy is the Barton decarboxylative coupling, comprising a one-pot radical decarboxylation and quinone addition cascade. The scalable synthesis of (+)-yahazunol was accomplished in five longest linear sequences (LLS) starting from commercially available and inexpensive (-)-sclareol. The divergent translational potential of (+)-yahazunol was demonstrated by the expedient preparation of (-)-zonarone, (-)-isozonarone, (-)-zonarol, (-)-isozonarol, (+)-chromazonarol, and (+)-yahazunone. This approach also enables the formal synthesis of puupehenol, puupehedione, and hongoquercin A. Antifungal evaluation was performed, and this represents the first biological profiles for (+)-yahazunone, (+)-8-O-acetylyahazunone, and (+)-8-O-acetylyahazunol. (+)-Chromazonarol and (+)-yahazunone are promising candidates against Sclerotinia scleotiorum, with EC50 values of 24.1 and 28.7 μM, respectively, demonstrating advantages over the original model (DM) and synthesized heterocyclic mimic (3a) of meroterpenoids. This will favor the establishment of a chemical repertoire in the management of different plant diseases.
Transition-metal-catalyzed allylic substitution and titanocene-catalyzed epoxypolyene cyclization as a powerful tool for the preparation of terpenoids
Gansaeuer, Andreas,Justicia, Jose,Rosales, Antonio,Worgull, Dennis,Rinker, Bjoern,Cuerva, Juan Manuel,Oltra, Juan Enrique
, p. 4115 - 4127 (2007/10/03)
Many biologically active substances are composed of sesquiterpene units linked to aromatic structures, especially substituted phenols. Here, we describe an efficient synthetic approach to this class of natural product from commercially available substances in a short sequence. The key transformations involve allylic substitution reactions using a palladium or copper catalyst and titanocene-catalyzed epoxypolyene cyclization reactions via radicals. The polycyclic core structures are accessed with high chemo- and stereocontrol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Highly efficient synthesis of the optically active sesquiterpene hydroquinone (+)-zonarol and the sesquiterpene quinone (+)-zonarone
Villamizar, Jose,Orcajo, Angel L.,Fuentes, Juan,Tropper, Eleonora,Alonso, Randolph
, p. 395 - 397 (2007/10/03)
A facile synthesis of the sesquiterpene hydroquinone (+)-zonarol 5 and sesquiterpene quinone (+)-zonarone 6 from manool is reported in 7 and 8 steps, respectively.