269409-17-8

Upstream product

• 269409-13-4 C₁₉H₃₀N₂O₄ 
• 214260-87-4 (1S,2R,6S,7R)-1,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide 
• 269409-12-3 (2Z)-3-amino-5-methyl-2,4-hexadienoic acid methyl ester 
• 4786-24-7 3,3-dimethylacrylonitrile 
• 269409-15-6 C₂₇H₃₈N₂O₆ 

Downstream Products

• 269409-19-0 (2S,3S)-3-Benzyloxycarbonylamino-2-(1-hydroxy-1-methyl-ethyl)-pentanedioic acid 5-methyl ester 
• 19427-85-1 (+)-2β-hydroxybornan-3-one 
• 269409-18-9 (3S,4S)-4-formyl-5-hydroxy-5-methyl-3-phenylmethyloxycarbonylamino hexanoic acid methyl ester 

Relevant academic research and scientific papers

Oxazoline N-oxide mediated [2 + 3] cycloadditions. Application to a formal synthesis of (+)-carpetimycin A.

[formula: see text] Cycloaddition between gamma,delta-unsaturated beta-enamino ester 9 and camphor-derived oxazoline N-oxide 8 afforded a single adduct, 14. Dipolarophile 9 proved to be very reactive despite the substitution on the double bond. Stereoselective sodium cyanoborohydride reduction of the imminium intermediate 14a gave rise stereoselectively to beta-amino ester derivative 15a. Oxidative acidic hydrolysis, oxidation of the resulting aldehyde 18, deprotection, and cyclization afforded the beta-lactam 23, a direct precursor of (+)-carpetimycin A.