3772-54-1

Upstream product

• 110530-31-9 O-Methyl-7-methyl-podocarpinal-semicarbazon 
• 109560-78-3 (+/-)-12-Methoxy-13-methyl-podocarpatrien-(8,11,13) 
• 107543-23-7 (+/-)-12-Methoxy-13-mercaptomethyl-5α-podocarpatrien-7-on 
• 578-58-5 2-methylmethoxybenzene 
• 472-68-4 (2,6,6-trimethylcyclohex-1-enyl)acetic acid 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 69919-95-5 2-(3-methyl-4-methoxyphenyl)ethyl bromide 
• 123060-88-8 (+/-)-12-hydroxy-13-dimethylaminopodocarpa-8,11,13-triene 
• 123060-89-9 ((4bR,8aR)-3-Hydroxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-ylmethyl)-trimethyl-ammonium; iodide 
• 15340-76-8 (4bR,8aR)-4b,8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol 
• 107782-35-4 (+/-)-12-Methoxy-13-chlormethyl-5α-podocarpatrienon-(7) 
• 104913-70-4 (+/-)-deoxynimbiol methyl ether 

Downstream Products

• 561-95-5 nimbiol 

Relevant academic research and scientific papers

Novel domino reactions for diterpene synthesis

New types of concerted domino acylation-cycloalkylation/alkylation- cycloacylation reactions have been described. These processes promoted by methanesulfonic acid-phosphorus pentoxide and concentrated H2SO 4, respectively, provide efficient, elegant, and expeditious routes for biologically active naturally occurring diterpenoids, namely (±)-ferruginol (1), (±)-nimbidiol (2), (±)-nimbiol (3), (±)-totarol (4), and ar-abietatriene (5).

Facile total synthesis of (±)-nimbiol

A facile total synthesis of (±)-nimbiol 1 has been achieved. In order to decrease the dioxo byproduct 2a, an improved oxidation system of CrO3/H2O/HOAc/NaOAc was used.

Facile transformation of 1-methoxynaphthalenes to octahydrophenanthrenes. Application to the total synthesis of (±)-sempervirol methyl ether, (±)-sugiol methyl ether, (±)-nimbiol methyl ether, and (±)-nimbidiol dimethyl ether

An efficient general method has been developed for the synthesis of the tricyclic aromatic ketones 4, 12, 13 and 14 from the 1-methoxynaphthalenes 8, 9, 10 and 11 respectively. The transformations of the ketones 4, 12, 13 and 14 into the diterpene ethers (±)-sempervirol methyl ether (7), (±)-sugiol methyl ether (15), (±)-nimbiol methyl ether (16), and (±)-nimbidiol dimethyl ether (17) have been successfully accomplished involving reductive methylation in liquid ammonia as the key reaction.

Total synthesis of (+/-)-nimbidiol dimethyl ether and (+/-)-nimbiol methyl ether

Steeocontrolled total syntheses of (+/-)-nimbidiol dimethyl ether (4) and (+/-)-nimbiol methyl ether (2) have been accomplished involving reductive methylation of the tricyclic aromatic ketones 11 and 12 respectively as the key steps.

INFLUENCE OF METHOXY- AND METHYL-AROMATIC SUBSTITUENS ON STEREOCHEMISTRY OF THE PRODUCTS IN THE ACID-CATALIZED CYCLIZATION OF 2-(2-ARYLETHYL)-1,3,3-TRIMETHYLCYCLOHEXANOLS: STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)- NIMBIDIOL AND (+/-)-NIMBIOL

The distributions of the trans- and the cis-podocarpatrienes (5c-g) and (6c-g) in the cyclialkylation reaction of the easily accesible cyclohexanols (4c-g) under a mild condition have been investigated.The cyclohexanol precursors having unactivated aromatic ring proceeds with high stereoselectivity leading to the respective trans-products, while the substrates with an electron donating methoxy or a methyl substituent with respect to the site of electrophilic attack result in the corresponding cis- and the trans-product mixtures.Consistent mechanisms for these stereochemical results have been advanced.Based on these results simple synthesis of the modified diterpenes (+/-)-nimbidiol (7) and (+/-)-nimbiolmethylether (18) have been realized.