39707-54-5

Upstream product

• 108944-92-9 (-)-zonarol dimethyl ether 
• 250146-77-1 Acetic acid [2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-methyl ester 
• 39707-56-7 (+)-zonarone 
• 63757-96-0 (+/-)-zonarol dimethyl ether 
• 596-85-0 (+)-manool 
• 3796-70-1 trans geranyl acetone 
• 56523-17-2 methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate 
• 108944-88-3 (1S,2S,4aS,8aS)-(-)-1-hydroxymethyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 108944-86-1 (1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 
• 1376654-39-5 borono-sclareolide 
• 86546-84-1 (5S,8R,10S)-drim-9⁽¹¹⁾-en-8-ol 
• 103476-92-2 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-ol 
• 57457-77-9 (+)-ent-chromazonarol 
• 564-20-5 (3aR)-(+)-sclareolide 

Downstream Products

• 39707-56-7 (+)-zonarone 
• 39707-56-7 (+)-zonarone 
• 69880-60-0 (+)-zonarol dimethyl ether 
• 455331-85-8 (+)-zonarol dibenzyl ether 
• 69809-36-5 yahazunol 
• 455331-86-9 (8R,S)-8,12-epoxyzonarol dibenzyl ether 
• 455331-88-1 (+)-yahazunol dibenzyl ether 

Relevant academic research and scientific papers

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.

Scalable, divergent synthesis of meroterpenoids via "borono- sclareolide"

A scalable, divergent synthesis of bioactive meroterpenoids has been developed. A key component of this work is the invention of "borono- sclareolide", a terpenyl radical precursor that enables gram-scale preparation of (+)-chromazonarol. Subsequent synthetic operations on this key intermediate permit rapid access to a variety of related meroterpenoids, many of which possess important biological activity.

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.

New access to sesquiterpene hydroquinones: Synthesis of (+)-ent-chromazonarol

A facile access to optically active (+)-ent-chromazonarol ent-1, isolated from the sponge Disidea pallescens, is reported from commercially available (+)-manool 4. Copyright Taylor & Francis LLC.

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.

Total synthesis of yahazunol, zonarone and isozonarone

The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol.

Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone

The total synthesis of the naturally occurring sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone was achieved starting from β-ionone, which was transformed via (+)-albicanic acid to (+)-albicanal and (-)-drim-7-en-11-al. Coupling of the aldehydes with lithiated hydroquinone ethers and further modification of the coupling products led to the target molecules. (C) 2000 Elsevier Science Ltd.

Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds

Efficient syntheses of ent-isozonarol (6a), ent-isozonarone (7a) and ent-chromazonarol (8) from (-)-sclareol (12) are described. 6a and 7a show a significative antitumoral activity.