72853-81-7

Basic information

• Product Name: (+)-Aureol
• Synonyms: (+)-Aureol;(1S)-1β,9aβ,14,14-Tetramethyl-4β,4aβ-butano-1,2,3,4,4a,9a-hexahydro-9H-xanthene-7-ol;(4aS,13aS)-4,4,7α,7aα-Tetramethyl-1,2,3,4,4aβ,5,6,7,7a,8-decahydrobenzo[d]xanthene-10-ol;(4aS,7aR,13aS)-1,2,3,4,4aβ,5,6,7,7a,8-Decahydro-4,4,7α,7aα-tetramethylbenzo[d]xanthen-10-ol;Aureol【terpene】
• CAS NO: 72853-81-7
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.4617
• Mol File: 72853-81-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Aureol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Aureol(72853-81-7)
• EPA Substance Registry System: (+)-Aureol(72853-81-7)

Safety Data

• Hazardous Substances Data: 72853-81-7(Hazardous Substances Data)

Upstream product

• 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 
• 55303-98-5 avarol 
• 129443-87-4 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol 

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 articles and documents

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.

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