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- Title
Construction of the Pentacyclic Core and Formal Total Synthesis of (rac)‐Renieramycin T.
- Authors
Kimura, Shinya; Saito, Naoki
- Abstract
Invited for this month's cover picture is the group of Professor Naoki Saito at the Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University (Japan). They achieved the first total synthesis of renieramycin T in 2016, and they have been following an alternative route to supply a large amount of it in order to promote research of the next stage, such as structure–activity relationship studies. This paper reports a formal total synthesis in 21 steps from a known piperazine‐2,5‐dione derivative. The key step of this synthesis is the modified Pictet–Spengler cyclization of a primary amine with an oxomalonic acid ester derivative followed by decarboxylation, and stereo‐controlled protonation at C‐1 position of the enol intermediate from the less‐hindered face. Read the full text of their Full Paper at 10.1002/open.201800112. "This research work consists of 1) isolation and structure elucidation with several collaborators in the Asian region to explore novel compounds as the seed of medicine, 2) synthetic study of isolated compounds and their derivatives, and 3) biological evaluation of natural and synthetic compounds. The aim is to be "germinated" as a seed of new medicine from the Asian sea through a powerful medicinal chemistry based on biologically active marine natural products in the Asian region...." Find out more about the story behind the front cover research at 10.1002/open.201800112.
- Subjects
CYCLIC compounds synthesis; STRUCTURE-activity relationship in pharmacology; DECARBOXYLATION; CHEMICAL derivatives; RING formation (Chemistry)
- Publication
ChemistryOpen, 2018, Vol 7, Issue 10, p753
- ISSN
2191-1363
- Publication type
Article
- DOI
10.1002/open.201800178