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

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

• 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 
• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 
• 52289-93-7 o-Methoxybenzyl bromide 
• 22418-80-0 3-oxopent-4-enoic acid ethyl ester 
• 3733-18-4 4a-methyl-2,5-dioxo-2,3,4,4a,5,6,7,8-octahydro-[1]naphthoic acid ethyl ester 
• 82273-33-4 C₁₆H₂₂O₅ 
• 62890-98-6 2,5-dimethoxyphenylmagnesium bromide 
• 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 
• 129443-87-4 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol 

Downstream Products

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

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.

New tools for studying vesicular-mediated protein trafficking: Synthesis and evaluation of ilimaquinone analogs in a non-radioisotope-based antisecretory assay

Structural variants of the marine sponge metabolite ilimaquinone, with comparable biological activity, have been prepared. These analogs, as well as related natural products, were screened for their effects on the Golgi apparatus through a novel, non-radioisotope-based secretion assay. The assay has identified a variant of ilimaquinone that contains a versatile linker group yet retains the natural product's cellular activity. This functional ilimaquinone analog will be a valuable tool for studying intracellular protein trafficking.

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.