150267-49-5

Upstream product

• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 100-39-0 benzyl bromide 
• 564-20-5 (3aR)-(+)-sclareolide 
• 100-44-7 benzyl chloride 
• 119987-19-8 isosclareyl diacetate 
• 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 
• 95169-56-5 13,14,15,16-tetranor-8-acetoxy-12-labdanal 
• 515-03-7 sclareol 
• 3649-91-0 8,15-dihydroxy-13E-labdane 
• 5153-92-4 sclareol oxide 

Downstream Products

• 150267-50-8 (4aS,5S,8aS)-5-(2-Benzyloxy-ethyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalene 
• 178394-54-2 C₂₃H₃₄O₂ 

Relevant academic research and scientific papers

Synthesis and structural revision of cyslabdan

Cyslabdan was isolated from the culture broth of Streptomyces sp. K04-0144 as a new potentiator of imipenem activity against methicillin-resistant Staphylococcus aureus. We accomplished the synthesis of cyslabdan according to a previously reported structure. However, we subsequently found that this structure was incorrect; our analysis of natural cyslabdan showed that it possessed R stereochemistry at the C8 position, not S, as had previously been reported. Thus, we completed the protecting-group-free synthesis of the correct structure of cyslabdan, which is described herein.

Bioactivity-guided mixed synthesis accelerate the serendipity in lead optimization: Discovery of fungicidal homodrimanyl amides

The bioactivity-guided mixed synthesis was conceived, in which the designed mix-reactions were run in parallel for simultaneous construction of different kinds of analogs. The valuable ones were protruded by biological screening. This tactic will facilitate more rapid incorporation of bioactive candidates into pesticide chemists' repertoire, exemplified by the optimization of less explored homodrimanes as antifungal ingredients. The discovery of D9 as a potent fungicidal agent can be completed in 50 of 3.33?mg/L and 2.45?mg/L against S.?sclerotiorum and B.?cinerea, respectively. To confirm the practicability, time-efficiency, and reliability, specific homodrimanes (82 derivatives) were synthesized and elucidated separately and determined for EC50 values. The SAR correlated well with the intentionally mixed synthesis and the potential was further confirmed by the in vivo bioassay. This methodology will foster more efficient exploration of biologically relevant chemical space of natural products in pesticide discovery, and can also be tailored readily for the lead optimization in medicinal chemistry.

Oxidative degradation of the sclareol side chain: hemisyntheses of ambergris derivatives using in the key steps palladium complexes or ruthenium tetroxide generated in situ

We report the hemisyntheses of various ambergris-type derivatives: ambraoxide 4, Ambrox 8, 13-methylambraoxide 13, ambraketal 14, norambraketal 15, non-norambraketal 16 and dioxepane 53.Sclareol 12 is used as starting material because it is currently available from Salvia sclarea.The key steps involve an oxidative degradation of the sclareol 12 side chain, using either palladium complexes or ruthenium tetroxide generated in situ. - Keywords: sclareol; Ambrox; ambraoxide; 13-methylambraoxide; ambraketal; norambraketal; nor-norambraketal; farnesylic aldehyde; palladium complex; ruthenium tetroxide generated in situ; oxidative degradation

Synthesis of norambracetal: A new ambergris derivative

We describe the synthesis of norambracetal 14 from sclareol 1 using γ-homobicyclofarnesilic aldehyde10 as a key intermediate.