1153-34-0

Upstream product

• 914799-48-7 C₁₈H₃₀O₂ 
• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 515-03-7 sclareol 
• 3910-88-1 C₁₈H₃₀O₂ 
• 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 

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.

Novel Diastereoselective Routes for the Synthesis of the Ambergris ketals

New processes have been developed which allow the stereoselective syntheses of the ambergris ketals 8α,13;13,17-diepoxi-14,15-dinorlabdane 1 and 8β,13;13,17-diepoxi-14,15-dinorlabdane 2, through selection of the appropriate catalyst for the δ,ε-epoxycarbonyl rearrangement of the key intermediate 3, which is, in turn, obtained by controlled oxidation of anticopalic acid 6.

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.