1376654-34-0

Basic information

• Product Name: (+)-yahazunone
• Synonyms: (+)-yahazunone
• CAS NO: 1376654-34-0
• Molecular Weight: 330.467
• Mol File: 1376654-34-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-yahazunone(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-yahazunone(1376654-34-0)
• EPA Substance Registry System: (+)-yahazunone(1376654-34-0)

Safety Data

• Hazardous Substances Data: 1376654-34-0(Hazardous Substances Data)

Upstream product

• 1376654-31-7 (1R,2R,4aS,8aS)-1-(iodoethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-yl formate 
• 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 
• 31207-65-5 8α-acetoxy-13,14,15,16-tetranor-12-labdanoic acid 
• 515-03-7 sclareol 
• 573983-71-8 isozonarone Δ^8,9 
• 573969-75-2 (4aS,8aS)-8-(2,5-Dimethoxy-benzyl)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 

Downstream Products

• 39707-56-7 (+)-zonarone 
• 39707-59-0 ent-isozonarone 
• 39707-54-5 (-)-ent-zonarol 
• 250146-75-9 ent-isozonarol 

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.

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.