39707-56-7

Basic information

• Product Name: 2-[[(1S,4aα)-2-Methylene-5,5,8aβ-trimethyldecahydronaphthalene-1-yl]methyl]-1,4-benzoquinone
• Synonyms: 2-[[(1S,4aα)-2-Methylene-5,5,8aβ-trimethyldecahydronaphthalene-1-yl]methyl]-1,4-benzoquinone;2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-2,5-cyclohexadiene-1,4-dione;Zonarone
• CAS NO: 39707-56-7
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.44582
• Mol File: 39707-56-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-[[(1S,4aα)-2-Methylene-5,5,8aβ-trimethyldecahydronaphthalene-1-yl]methyl]-1,4-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[(1S,4aα)-2-Methylene-5,5,8aβ-trimethyldecahydronaphthalene-1-yl]methyl]-1,4-benzoquinone(39707-56-7)
• EPA Substance Registry System: 2-[[(1S,4aα)-2-Methylene-5,5,8aβ-trimethyldecahydronaphthalene-1-yl]methyl]-1,4-benzoquinone(39707-56-7)

Safety Data

• Hazardous Substances Data: 39707-56-7(Hazardous Substances Data)

Upstream product

• 39707-54-5 (-)-ent-zonarol 
• 63757-96-0 (+/-)-zonarol dimethyl ether 
• 915304-99-3 3-[(3E,7E)-9-(2,5-Dimethoxy-phenyl)-3,7-dimethyl-nona-3,7-dienyl]-2,2-dimethyl-oxirane 
• 29442-57-7 10,11-epoxy-3,7,11-trimethyl-2,6-dodecadien-1-ol acetate 
• 62890-98-6 2,5-dimethoxyphenylmagnesium bromide 
• 166900-19-2 C₁₅H₂₄O 
• 39707-54-5 (+)-zonarol 
• 56523-17-2 methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate 
• 108888-69-3 (1R,4aR,8aR)-(+)-1-(p-tosyloxy)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 3796-70-1 trans geranyl acetone 
• 59633-93-1 (1S,4aS,8aS)-(-)-1-(p-tosyloxy)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 59633-90-8 (4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone 
• 478930-77-7 [2,5-bis-(tetrahydro-pyran-2-yloxy)-phenyl]-(5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-methanol 
• 478930-78-8 (-)-ent-zonarol di-THP ether 

Downstream Products

• 455331-88-1 (+)-yahazunol dibenzyl ether 
• 455331-86-9 (8R,S)-8,12-epoxyzonarol dibenzyl ether 
• 455331-85-8 (+)-zonarol dibenzyl ether 
• 69809-36-5 yahazunol 
• 39707-54-5 (+)-zonarol 
• 39707-54-5 (-)-ent-zonarol 
• 69880-60-0 (+)-zonarol dimethyl ether 

Relevant articles and documents

Expediently Scalable Synthesis and Antifungal Exploration of (+)-Yahazunol and Related Meroterpenoids

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

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

A facile synthesis of the sesquiterpene hydroquinone (+)-zonarol 5 and sesquiterpene quinone (+)-zonarone 6 from manool is reported in 7 and 8 steps, respectively.