The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N
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چکیده
منابع مشابه
The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N
Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels-Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a on...
متن کاملTotal synthesis of (-)-calyciphylline N.
The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenati...
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Three new Daphniphyllum alkaloids, daphnioldhanins A-C (1-3), along with four known ones, were isolated from the aerial parts of saplings of Daphniphyllum oldhami. The structures of these alkaloids were established by spectroscopic methods. The relative configuration of 1 was further confirmed by a single-crystal X-ray diffraction analysis. In addition, the (1)H and (13)C NMR data of the free b...
متن کاملFive new alkaloids from the stem bark of Daphniphyllum macropodum.
Five new alkaloids, daphnicyclidins M and N (compounds 1 and 2) and calyciphyllines Q-S (compounds 3-5), along with four known ones, paxiphylline C (6), macropodumine B (7), macropodumine C (8) and daphnicyclidin A (9) were isolated from the stem bark of Daphniphyllum macropodum. Calyciphylline Q (3) is the first calyciphylline A derivative possessing a double bond between C-18 and C-19. Their ...
متن کاملRapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical
A streamlined approach to the tertiary amine-containing core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids is presented. A known carvone derivative is converted into the core structure in only four synthetic operations, and it is well poised for further elaboration. The key enabling methodology is a radical cyclization cascade beginning with addition of a secondary, ...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2015
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja503899t