130288-22-1

Usage

InChI:InChI=1/C16H22N2O3/c1-12(14(19)16(2,3)15(17)20)8-6-4-5-7-9-13-10-18-11-21-13/h4-8,10-11,14,19H,9H2,1-3H3,(H2,17,20)/b6-4-,7-5+,12-8-/t14-/m1/s1

Upstream product

• 149694-63-3 (Z)-2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-ol 
• 1332721-85-3 (3S,4S)-3-methyl-4-((Z)-5-(trimethylsilyl)pent-2-en-4-yn-2-yl)-oxetan-2-one 
• 1332721-86-4 (2S,3S,4Z)-methyl 3-hydroxy-2,4-dimethyl-7-(trimethylsilyl)hept-4-en-6-ynoate 
• 1332721-87-5 (R,Z)-methyl 3-hydroxy-2,2,4-trimethyl-7-(trimethylsilyl)hept-4-en-6-ynoate 
• 127232-37-5 (R,Z)-methyl 3-hydroxy-2,2,4-trimethylhept-4-en-6-ynoate 
• 127232-44-4 (R,4Z,6Z,8E)-methyl 3-((tert-butyldimethylsilyl)oxy)-2,2,4-trimethyl-10-(oxazol-5-yl)deca-4,6,8-trienoate 
• 127232-45-5 (R,4Z,6Z,8E)-methyl 3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)deca-4,6,8-trienoate 
• 127232-47-7 (R,4Z,6Z,8E)-3-acetoxy-2,2,4-trimethyl-10-(oxazol-5-yl)deca-4,6,8-trienoic acid 
• 127232-40-0 (R,4Z,6Z)-methyl 3-(tert-butyldimethylsilyl)oxy-7-iodo-2,2,4-trimethylhepta-4,6-dienoate 
• 127232-39-7 (R,Z)-methyl 3-((tert-butyldimethylsilyl)oxy)-7-iodo-2,2,4-trimethylhept-4-en-6-ynoate 
• 127232-38-6 methyl (3R,4Z)-3-[(tert-butyldimethylsilyl)oxy]-2,2,4-trimethylhept-4-en-6-ynoate 
• 127232-46-6 (4Z,6Z,8E)-(R)-3-Hydroxy-2,2,4-trimethyl-10-oxazol-5-yl-deca-4,6,8-trienoic acid 
• 127232-31-9 (Z)-2-methyl-5-(trimethylsilyl)pent-2-en-4-ynal 
• 35042-52-5 (E)-2-penten-4-yn-1-ol 

Downstream Products

• 132911-60-5 3-O-<(S)-2-Phenylbutyryl>inthomycin 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Inthomycins A, B, and C

Herein, we report the asymmetric total syntheses of inthomycin antibiotics containing a methylene-interrupted oxazolyl-triene motif. Utilizing the α,β-unsaturated aldehyde as a common intermediate, all three inthomycins A-C were divergently synthesized. The asymmetric ynone reduction provided an R-configured secondary alcohol as in the natural products with high enantioselectivity. The geometrically different triene units for each inthomycin were stereoselectively established via methyl cuprate conjugate addition, isomerization of the α,β-unsaturated aldehyde intermediate, and stereoretentive cross-coupling reactions.

Short, Tin-Free Synthesis of All Three Inthomycins

The inthomycins are a family of structurally and biologically rich natural products isolated from Streptomyces species. Herein the implementation of a modular synthetic route is reported that has enabled the enantioselective synthesis of all three inthomycins. Key steps include Suzuki and Sonogashira cross-couplings and an enantioselective Kiyooka aldol reaction.

Organocatalytic asymmetric syntheses of inthomycins A, B and C

The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric β-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.