406684-19-3

Upstream product

• 1235459-89-8 (2R,6R)-2-(benzyloxymethyl)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran 
• 380355-90-8 ((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)methanol 
• 130856-15-4 (+)-(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl carboxylic acid 
• 90344-49-3 (2R)-3-iodo-2-methylpropyl benzyl ether 
• 406684-16-0 (S)-4-Benzyl-3-[(R)-2-((R)-1-ethyl-2-methyl-allyloxy)-pent-4-enoyl]-oxazolidin-2-one 
• 406684-15-9 (S)-4-Benzyl-3-[2-((R)-1-ethyl-2-methyl-allyloxy)-acetyl]-oxazolidin-2-one 
• 406684-14-8 ((R)-1-Ethyl-2-methyl-allyloxy)-acetic acid 
• 125637-07-2 (R)-3-hydroxy-2-methylpent-1-ene 
• 406684-17-1 (S)-4-Benzyl-3-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-carbonyl)-oxazolidin-2-one 

Downstream Products

• 58857-02-6 (+)-ambruticin S 
• 130799-17-6 methyl 5β,6α-dibenzyloxypolyangioate 
• 406684-20-6 5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.