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A concise synthesis of tubuphenylalanine and epi-tubuphenylalanine via a diastereoselective Mukaiyama aldol reaction of silyl ketene acetal

Title
A concise synthesis of tubuphenylalanine and epi-tubuphenylalanine via a diastereoselective Mukaiyama aldol reaction of silyl ketene acetal
Authors
Park, YunjeongSim, MikyungChang, Tong-ShinRyu, Jae-Sang
Ewha Authors
창동신류재상
SCOPUS Author ID
창동신scopus; 류재상scopus
Issue Date
2016
Journal Title
ORGANIC & BIOMOLECULAR CHEMISTRY
ISSN
1477-0520JCR Link1477-0539JCR Link
Citation
vol. 14, no. 3, pp. 913 - 919
Publisher
ROYAL SOC CHEMISTRY
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
We have developed a straightforward and auxiliary-free synthetic route towards tBu-tubuphenylalanine (tBu-Tup) and tBu-epi-tubuphenylalanine (tBu-epi-Tup), which are the key components of tubulysins and their analogs. A Lewis acid-mediated diastereoselective Mukaiyama aldol reaction using silyl ketene acetal and N-Boc-L-phenylalaninal provided gamma-amino-beta-hydroxyl-alpha-methyl esters, which were deoxygenated to gamma-amino-alpha-methyl esters under Barton-McCombie deoxygenation conditions. Notably, the desired tBu-Tup and tBu-epi-Tup were obtained in good overall yields in four steps.
DOI
10.1039/c5ob02239h
Appears in Collections:
약학대학 > 약학과 > Journal papers
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