A general enantioselective O-2-isocephem synthesis

Mastalerz, Harold; Vinet, V.

doi:10.1039/c39870001283

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2017

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Cited by 18 publications

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“…Removal of Boc group in 17 (TFA) and subsequent N , N -dimethylation by reductive amination [40% HCHO aqu., NaBH 3 (CN)] generated the desired N,N -dimethyl amino ester 4 (64%, two steps). 14 The Pd-catalyzed deprotection of the O -allyl group in 4 [Pd(PPh 3 ) 4 , N -methylaniline, NMA] afforded the corresponding free acid, 15 which was used to acylate Tyr-OBn ( 5 , HATU, HOAt, DIPEA) and deliver linear peptide 18 (45%, two steps). 10a,d Deprotection of the benzyl ester 18 (H 2 , 1 atm, Pd/C) gave the free acid 19 in quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and structure revision of symplocin A

Shao

Mao

et al. 2017

Org. Chem. Front.

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Symplocin A, a linear peptide possessing N-terminal N,N-dimethylisoleucine, statine, and valic acid residues, has been synthesized for the first time employing our previously established ‘one-pot intramolecular tandem protocol’. Moreover, the stereochemistry of natural symplocin A was unambiguously revised through the confirmation by 1D NMR, 2D NMR, and HPLC comparisons with authentic natural product.

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Section: Resultsmentioning

confidence: 99%