184485-46-9

Upstream product

• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 61950-54-7 (8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 41722-49-0 (S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 

Downstream Products

• 184485-47-0 (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone 
• 237735-94-3 C₂₄H₃₆O₄ 
• 237735-96-5 (1R,2R,4aS,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene 
• 237735-97-6 2-((1R,2R,4aS,8aS)-1,2,4a-Trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-benzene-1,4-diol 
• 237736-01-5 2-((1R,2R,4aS,8aS)-1,2,4a-Trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,4]benzoquinone 
• 237735-95-4 (4aS,5R,6R,8aS)-5-(2,5-Dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one 
• 184485-48-1 (1S,2S,4aS)-(-)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-5-(2-methyl-1,3-dioxolan-2-yl)-octahydro-1β,2β,4aβ-trimethyl-5(6H)-naphthalenone 
• 274900-31-1 (4aS,5S,8aS)-5-(2,5-Dimethoxy-benzyl)-5,8a-dimethyl-6-methylene-octahydro-naphthalen-1-one 
• 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 
• 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 
• 55303-98-5 avarol 
• 55303-99-6 avarone 
• 61187-42-6 avarol dimethyl ether 

Relevant academic research and scientific papers

Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, synthesis of cis-decalin 2 and trans-decalin 3 was carried out. Comparison of NMR spectra of 2 and 3 with that of akaterpin indicated that the upper decalin has a cis-fused structure.

Enantiospecific total synthesis of (+)- and (-)-avarone and -avarol

Enantiopure avarol and its oxidized congener avarone are synthesized in both podal series from an optically pure Wieland-Miescher enone; preliminary results from biochemical studies are summarized.

Stereoselective synthesis of (+)-avarol, (+)-avarone, and some nonracemic analogues

Synthesis of the rearranged drimane sesquiterpenoids (+)-avarol and (+)-avarone from Wieland-Miescher ketone is described. This synthetic sequence provides convenient access to the natural enantiomers and, based on comparison of the optical rotation of synthetic avarol dimethyl ether with literature data, affords material of significantly higher optical rotation than a natural source. Similar synthetic strategies have been used to obtain several related compounds, including a decalin bearing an exocyclic olefin and a highly substituted cyclohexane, that can be viewed as hybrids of the trans-fused avarol and cis-fused arenarol skeletons.