85541-57-7Relevant academic research and scientific papers
New building block for polyhydroxylated piperidine: Total synthesis of 1,6-dideoxynojirimycin
Rengasamy, Rajesh,Curtis-Long, Marcus J.,Woo, Duck Seo,Seong, Hun Jeong,Jeong, Ill-Yun,Ki, Hun Park
, p. 2898 - 2901 (2008/09/19)
(Chemical Equation Presented) (3R,4S)-3-Hydroxy-4-N-allyl-N-Boc-amino-1- pentene 10, an important precursor for the synthesis of polyhydroxylated piperidines, has been achieved as a single diastereomer without racemization via vinyl Grignard addition to N-Boc-N-allyl aminoaldehyde 9, which was derived from an enantiopure natural amino acid. Having forged a tetrahydropyridine ring scaffold 13 from 10 in 85% yield via RCM using Grubbs II catalyst, we were able to effect its stereodivergent dihydroxylation, via a common epoxide intermediate to yield a range of interesting hydroxylated piperidines, including ent-1,6-dideoxynojirimycin (ent-1,6-dDNJ) 1 (28% overall yield) and 5-amino-1,5,6-trideoxyaltrose 2 (29% over all yield) in excellent dr. To the best of our knowledge, our synthesis of ent-1,6-dDNJ 1 is the most expeditious to date.
Improved stereoselectivity in intramolecular SN2′ cyclization through use of mechanistic principles
Woo, Duck Seo,Curtis-Long, Marcus J.,Seong, Hun Jeong,Tae, Hong Jun,Min, Suk Yang,Ki, Hun Park
, p. 209 - 214 (2007/10/03)
Valine and alanine were converted into the corresponding α-hydroxy-β-amino acids through intramolecular SN2′ cyclization. The novel cyclization protocol relied upon the use of N-benzyl-protected carbamates derived from α-amino acids. Georg Thie
Total synthesis of amamistatin A, an antiproliferative linear peptide from an actinomycete
Yokokawa, Fumiaki,Izumi, Kentaro,Omata, Junko,Shioiri, Takayuki
, p. 3027 - 3034 (2007/10/03)
Amamistatin A, a linear lipopeptide and a growth inhibitor of human tumor cell lines from an actinomycete, was efficiently synthesized by a convergent approach. The asymmetric synthesis of β-hydroxy acid fragment was achieved by using chiral oxazaborolidinone mediated aldol reaction. The oxazole ring was constructed from N-acylthreonine via side-chain oxidation and cyclodehydration. The synthesis of the linear peptide was carded out in a stepwise manner from the cyclic hydroxamic acid fragment, and the final deprotection provided amamistatin A. (C) 2000 Elsevier Science Ltd.
