76215-30-0

Upstream product

• 91178-22-2 1-Bromo-8-ketoambliol Acetate 
• 132912-33-5 <3-(3-Furyl)propyl>triphenylphosphonium Bromide 
• 24163-93-7 farnesyl bromide 
• 31499-72-6 7,8-dihydro-α-ionone 
• 105631-15-0 13-(p-toluenesulfonyl)ambliofuran 

Downstream Products

• 114350-44-6 4-[(E)-6-((1S,2S)-2-Hydroxy-2,6,6-trimethyl-cyclohexyl)-4-methyl-hex-3-enyl]-5-(2,2,6,6-tetramethyl-piperidin-1-yl)-5H-furan-2-one 
• 114301-61-0 15-(trimethylsilyl)ambliol A 
• 114301-62-1 16-(trimethylsilyl)ambliol A 
• 76249-87-1 5,18-dehydroambliol A 
• 114350-11-7 5-[(E)-6-((1S,2S)-2-Hydroxy-2,6,6-trimethyl-cyclohexyl)-4-methyl-hex-3-enyl]-2,6-dioxa-bicyclo[3.1.0]hexan-3-one 
• 114301-67-6 (1S,2S)-1,3,3-Trimethyl-2-[(E)-3-methyl-6-(3,5,7-trioxa-tricyclo[4.1.0.0^2,4]hept-1-yl)-hex-3-enyl]-cyclohexanol 
• 114301-66-5 4-[(E)-6-((1S,2S)-2-Hydroxy-2,6,6-trimethyl-cyclohexyl)-4-methyl-hex-3-enyl]-2,6-dioxa-bicyclo[3.1.0]hexan-3-one 
• 114301-64-3 15,16-dihydro-15-hydroxy-16-oxoambliol A 
• 114301-63-2 15,16-dihydro-16-hydroxy-15-oxoambliol A 

Relevant academic research and scientific papers

First enantioselective synthesis of marine diterpene ambliol-A

The first enantioselective synthesis of furanditerpene ambliol-A, which is a major metabolite of marine sponge Dysidea amblia, has been accomplished by starting from racemic α-ionone. The key steps of the synthesis include lipase-mediated resolution of 4-hydroxy-γ-ionone, its stereoselective transformation into trans-α-epoxy-dihydroionone, C2 homologation to trans-α-epoxy-monocyclofarnesyl acetate and Li2CuCl4-catalysed sp3-sp3 cross-coupling reaction of the latter ester with (furan-3-ylmethyl)magnesium chloride. This work confirms the chemical structure previously assigned to ambliol-A and proves that the natural levorotatory isomer does not possess (1S,2S) absolute configuration, as previously indicated, but is the opposite enantiomer, (1R,2R)-2-[(E)-6-(furan-3-yl)-3-methylhex-3-enyl]-1,3,3-trimethylcyclohexanol.

Studies on furoterpenes: Stereoselective total synthesis of (±)-ambliol-A and dendrolasin

(±)-Ambliol-A (1) is totally synthesised with high stereoselectivity starting from α-ionone and 13-(3'-furyl)propyl]triphenylphosphonium bromide (3). In another attempt utilising 3 with the commercially available ketone 11 the total synthesis of Dendrolasin (12) has also been achieved.

Biomimetic Cyclization of Ambliofuran and Analog By Using Mercury(II) Triflate/N,N-Dimethylaniline Complex: Synthesis of (+/-)-Ambliol-A

Biomometic cyclization of ambliofuran with mercury(II) triflate/N,N-dimethylaniline complex is initiated from the internal double bound (Δ7) in high selectivity, whereas the corresponding sulfone is cyclized from terminal (Δ15) olefin to give marginatan skeleton.

Metabolites of the Marine Sponge Dendrilla sp.

The sponge Dendrilla sp. was collected from a marine lake in Palau, Western Caroline Islands.Dendrilla sp. contained the known diterpenes dehydroambliol A (1) and norrisolide (2), together with the novel metabolites 1-bromo-8-ketoambliol A acetate (3), dendrillolide A (4), dendrillolide B (5), and dendrillolide C (6).The structures of the new metabolites were determined by interpretation of spectral data, application of a biosynthetic hypothesis, and chemical interconversions.