129445-46-1

Basic information

• Product Name: (-)-Neoavarone
• Synonyms: (-)-Neoavarone;2-[[[(1R,8aα)-Decahydro-1,2β,4aβ-trimethyl-5-methylenenaphthalen]-1α-yl]methyl]-2,5-cyclohexadiene-1,4-dione;Isoavarone;Neoavarone
• CAS NO: 129445-46-1
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.44582
• Mol File: 129445-46-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Neoavarone(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Neoavarone(129445-46-1)
• EPA Substance Registry System: (-)-Neoavarone(129445-46-1)

Safety Data

• Hazardous Substances Data: 129445-46-1(Hazardous Substances Data)

Upstream product

• 82273-33-4 C₁₆H₂₂O₅ 
• 62890-98-6 2,5-dimethoxyphenylmagnesium bromide 
• 3733-18-4 4a-methyl-2,5-dioxo-2,3,4,4a,5,6,7,8-octahydro-[1]naphthoic acid ethyl ester 
• 22418-80-0 3-oxopent-4-enoic acid ethyl ester 
• 184485-49-2 (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoyphenyl)methyl]-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalen-5-one 
• 481656-21-7 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one-5-ethyleneacetal 
• 481656-19-3 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal 
• 481656-23-9 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one 
• 481656-15-9 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-5-(methylene)decahydronaphthalene 
• 481656-25-1 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one 
• 52289-93-7 o-Methoxybenzyl bromide 
• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 
• 184485-50-5 (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene 
• 129443-87-4 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol 

Downstream Products

• 87764-13-4 (+/-)-Arenarol 
• 129443-87-4 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol 

Relevant articles and documents

Highly Improved Synthesis of (+)-Aureol via (-)-Neoavarone and (-)-Neoavarol, by Employing Salcomine Oxidation and Acid-Induced Rearrangement/Cyclization Strategy

A short and efficient synthesis of (+)-aureol (1), a structurally novel and biologicaly important marine natural product, was achieved starting with readily available (+)-Wieland-Miescher ketone analogue 7 via (-)-neoavarone (10) and (-)-neoavarol (11). The method features salcomine oxidation of the phenol derivative 9 to deliver 10 and BF3*OEt2-induced rearrangement/cyclization reaction of 11 to produce 1 as the crucial steps. The improvement biomimetic synthesis required only 9 steps and proceeds in 31 percent overall yield.

Application of the Nickel-Mediated Neopentyl Coupling in the Total Synthesis of the Marine Natural Product Arenarol

Racemic arenarol (1) has been synthesized from the known decalin 5β-carbethoxy-1,1-(1,2-ethylenedioxy)-5α,8aβ-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-oxonaphthalene (9) via a short, efficient, and highly stereocontrolled sequence.Key steps in this synthesis are the directed hydrogenation of an unsaturated neopentyl alcohol to provide stereocontrolled formation of the two adjacent tetriary centers and subsequent elaboration of the arenarol skeleton via a nickel-mediated coupling of the corresponding neopentyl iodide.This sequence demonstrates the value of nickel-mediated crosscoupling reactions for carbon-carbon bond formation at neopentyl centers.