57345-19-4

Usage

Chemical Properties

Dodecahydro-3,8,8,11a-tetramethyl-5H-3,5a-epoxynaphth[2,1-c]oxepin is a colorless to pale yellow liquid. It possesses a powerful amber note with good stability in nonaggressive media.

Preparation

The synthesis starts from the natural raw material manool, which is obtained by extraction from a tree growing in New Zealand, the so-called pink pine, Halocarpus biformis (Hooker) C.J. Quinn. Epoxidation of manool, subsequent oxidative degradation of the allylalcohol side chain to yield a ketone, and intramolecular acetalization afford the ketal.

Trade name

Ambermore Ketal (Aromor), Amberketal (Givaudan), Z11 (Firmenich).

InChI:InChI=1/C18H30O2/c1-15(2)8-5-9-16(3)13(15)7-11-18-12-19-17(4,20-18)10-6-14(16)18/h13-14H,5-12H2,1-4H3

Upstream product

• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 515-03-7 sclareol 
• 6466-98-4 sclareol 
• 119987-19-8 Acetic acid (1S,2S,4aR,8aR)-1-((E)-5-acetoxy-3-methyl-pent-3-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yl ester 
• 133661-27-5 Acetic acid (1S,2S,4aR,8aR)-2,5,5,8a-tetramethyl-1-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-decahydro-naphthalen-2-yl ester 
• 80098-20-0 Acetic acid (1S,2S,4aR,8aR)-2,5,5,8a-tetramethyl-1-(3-oxo-butyl)-decahydro-naphthalen-2-yl ester 
• 67987-70-6 2-Methyl-2-[2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxolane 
• 10266-75-8 15,16-Dinorlabd-8⁽¹⁷⁾-en-13-on 
• 133661-28-6 (1S,2S,4aR,8aR)-2,5,5,8a-Tetramethyl-1-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-decahydro-naphthalen-2-ol 
• 54274-72-5 (R)-5-((1R,2R,4aS,8aS)-2-acetoxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl acetate 
• 22628-62-2 8α-acetoxy-13R-hydroxy-labda-14-ene 
• 80098-20-0 8α-(acetyloxy)-14,15-dinorlabdan-13-one 
• 914799-48-7 C₁₈H₃₀O₂ 
• 3910-88-1 C₁₈H₃₀O₂ 

Relevant academic research and scientific papers

A short efficient synthesis of ambraketal (four steps) and epiambraketal (five steps) from sclareol

Ambraketal 7 and epiambraketal 8 are synthesized efficiently from sclareol 1. The key intermediate 5 is obtained by a regioselective elimination of ketoacetate 4 resulting from the side chain oxidative degradation of 1 by ruthenium tetroxide generated in situ.

SYNTHESIS OF AMBRACETAL AND EPI-8-AMBRACETAL

A protection-deprotection sequence is used in order to control the formation of the exocyclic double bond of compound 10 which is further used for the synthesis of the title compounds.