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- Title
Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization.
- Authors
Xi, Yong‐Kai; Zhang, Hongbin; Li, Rui‐Xi; Kang, Shi‐Yuan; Li, Jin; Li, Yan
- Abstract
Cyclodipeptide 2,5‐diketopiperazines (DKP) are privileged structural units present in drugs and natural alkaloids. This work reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic α‐addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l‐glutamic acid is highlighted by its application to the concise total syntheses of 6‐methoxyspirotryprostatin B (the first total synthesis), spirotryprostatin A, and spirotryprostatin B. Alkaloid synthesis: This work reports a concise and practical approach towards the synthesis of spirotryprostatins. This synthetic route features an organo‐mediated intramolecular umplolung cyclization to construct the DKP ring system, a Grignard addition‐dehydration‐Friedel–Crafts reaction procedure to establish the C‐ring and the prenyl moiety, and a regioselective oxidation and microwave‐assisted stereospecific rearrangement to afford the spiro‐oxindole system.
- Subjects
ALKALOID synthesis; INTRAMOLECULAR forces; RING formation (Chemistry); PIPERAZINE; NUCLEOPHILIC addition (Chemistry); AMIDES
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 12, p3005
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.201806411