72853-81-7

Upstream product

• 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 
• 1395881-49-8 C₁₆H₂₈O₂ 
• 1395881-47-6 C₁₆H₂₆ 
• 1395881-46-5 C₂₂H₃₁NO₂Se 
• 122508-18-3 (1R,2S)-1-(2-hydroxyethyl)-1,2,5,5-tetramethyl-Δ^4a(8a)-octahydronaphthalene 
• 64061-39-8 (1R,2R,4aS,8aS)-(+)-1-(2'-acetoxyethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene 
• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 564-20-5 (3aR)-(+)-sclareolide 
• 72853-85-1 2-((1R,2S)-1,2,5,5-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-benzene-1,4-diol 
• 1395881-52-3 C₃₃H₅₈O₂Si₂ 
• 1395881-51-2 C₃₃H₅₈O₃Si₂ 
• 1395881-50-1 C₁₅H₂₄O 
• 1395881-48-7 C₂₃H₃₄O 

Downstream Products

• 72853-86-2 (1R,2S)-1-(2,5-Dimethoxy-benzyl)-1,2,5,5-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalene 
• 72853-85-1 2-((1R,2S)-1,2,5,5-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-benzene-1,4-diol 
• 127707-56-6 (+)-5-epi-aureol 
• 72853-84-0 Acetic acid 4-acetoxy-2-((1R,2S)-1,2,5,5-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-phenyl ester 

Relevant academic research and scientific papers

Total synthesis of (+)-aureol

A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimet

Total synthesis of (+)-aureol

A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimet

Highly efficient total synthesis of the marine natural products (+)-avarone, (+)-avarol, (-)-neoavarone, (-)-neoavarol and (+)-aureol

Biologically important and structurally unique marine natural products avarone (1), avarol (2), neoavarone (3), neoavarol (4) and aureol (5), were efficiently synthesized in a unified manner starting from (+)-5-methyl-Wieland- Miescher ketone 10. The synthesis involved the following crucial steps: i) Sequential BF3·Et2O-in-duced rearrangement/ cyclization reaction of 2 and 4 to produce 5 with complete stereoselectivity in high yield (2 → 5 and 4 → 5); ii) strategic salcomine oxidation of the phenolic compounds 6 and 8 to derive the corresponding quinones 1 and 3 (6 → 1 and 8 →3); and iii) Birch reductive alkylation of 10 with bromide 11 to construct the requisite carbon framework 12 (10 + 11 → 12). An in vitro cytotoxicity assay of compounds 1-5 against human histiocytic lymphoma cells U937 determined the order of cytotoxic potency (3 > 1 > 5 > 2 > 4) and some novel aspects of structure-activity relationships.

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.

An efficient synthesis of (+)-aureol via boron trifluoride etherate-promoted rearrangement of (+)-arenarol

A novel marine natural product, (+)-aureol (1), was efficiently synthesized starting from the cis-fused decalin derivative 4. The synthetic method features boron trifluoride etherate-promoted rearrangement/cyclization reaction of (+)-arenarol (2) to form

Marine Sesquiterpene Quinones and Hydroquinones: Acid-Catalysed Rearrangements and Stereochemical Investigations

Acid treatment of both ilimaquinone (3) and 5-epi-ilimaquinone (9) yielded the same rearrangement products, (7) and (8), thus defining a common absolute stereochemistry.Likewise, acid-catalysed rearrangement of avarol (10) and arenarol (11) yielded the common product aureol (13), allowing the absolute stereochemistry of arenarol (11) and its related quinone arenarone (12) to be assigned.This latter acid-catalysed rearrangement also yielded an unexpected electrophilic aromatic cyclization product (15), the dimethyl ether (17) of which could be obtained in quantitative yield from acid treatment of avarol dimethyl ether (16).