214900-85-3

Upstream product

• 136897-84-2 (2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-ethyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 2-trimethylsilanyl-ethyl ester 
• 1194-02-1 4-fluorobenzonitrile 
• 214596-90-4 ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester 
• 214596-87-9 [2R,3S]-2-amino-4-methyl-1-(tetrahydropyran-2-yloxy)pentan-3-ol 
• 214596-86-8 (4R,5S)-5-Isopropyl-4-(tetrahydro-pyran-2-yloxymethyl)-oxazolidin-2-one 
• 3397-35-1 Z-L-leucine hydroxysuccinimide ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 136983-35-2 (R)-4-((S)-1-Hydroxy-2-methyl-propyl)-oxazolidin-2-one 
• 136898-38-9 (2S,3S)-3-(4-{2-Benzyloxycarbonyl-2-[(Z)-hydroxyimino]-acetyl}-phenoxy)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 2-trimethylsilanyl-ethyl ester 
• 136898-37-8 (2S,3S)-3-[4-(2-Benzyloxycarbonyl-acetyl)-phenoxy]-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 2-trimethylsilanyl-ethyl ester 
• 136898-39-0 (2S,3S)-3-[4-(2-Amino-1-hydroxy-ethyl)-phenoxy]-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 2-trimethylsilanyl-ethyl ester 
• 136898-36-7 4-{(S)-1-[(S)-tert-Butoxycarbonylamino-(2-trimethylsilanyl-ethoxycarbonyl)-methyl]-2-methyl-propoxy}-benzoic acid 
• 136898-35-6 4-{(S)-1-[(S)-tert-Butoxycarbonylamino-(2-trimethylsilanyl-ethoxycarbonyl)-methyl]-2-methyl-propoxy}-benzoic acid tert-butyl ester 
• 40361-27-1 Toluene-4-sulfonic acid (2R,3S)-2-benzyloxycarbonylamino-3-hydroxy-4-methyl-pentyl ester 

Downstream Products

• 214900-86-4 (2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-ethyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid pentafluorophenyl ester 
• 25350-22-5 frangulanine 
• 136898-43-6 [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthetic studies of 14-membered cyclopeptide alkaloids

A strained 14-membered cyclopeptide was prepared from the Garner aldehyde derived from D-serine. The key steps in the synthesis were the construction of the alkyl-aryl ether linkage via an S(N)Ar reaction involving 4-fluorobenzonitrile and the macrolactamization using a modification of the Schmidt protocol involving an activated pentafluorophenyl ester.

Total synthesis of the cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer

The naturally occurring cyclopeptide alkaloid sanjoinine G1 and its C- 11 epimer were synthesized in 18 steps from D-serine. The key steps in the synthesis were the formation of the alkylaryl ether linkage via an S(N)Ar reaction with 4-fluorobenzonitrile

Total Synthesis of Sanjoinine-G1

Sanjoinine-G1 (1), a 14-membered cyclopeptide, was synthesized with stereoselective reactions.Started from D-serine, a cyclic precursor for various frangulanine type 14-membered cyclopeptide alkaloids was synthesized and the side chain acylation product was identical with the natural sanjonine-G1 (17 steps, overall yield 1.36percent).

The Total Synthesis of Frangulanine

The reported preparation of the p-ansa compound frangulanine, previously isolated from Rhamnus frangula L., also constitutes the first total synthesis of a fourteen-membered cyclopeptide alkaloid.