Journal ArticleDOI
Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A-Type Alkaloids via Intramolecular [3+2] Cycloaddition
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TLDR
Asymmetric synthesis of the [5-6-7] tricyclic system common to the Calyciphylline A-type alkaloids is reported, featuring Overman rearrangement, Heck cyclization, intramolecular [3 + 2] cycloaddition, diastereoselective hydrogenation, and Claisen rearrangements as strategic events.About:
This article is published in Organic Letters.The article was published on 2014-02-07. It has received 36 citations till now. The article focuses on the topics: Overman rearrangement & Claisen rearrangement.read more
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Recent Progress in the Chemistry of Daphniphyllum Alkaloids
TL;DR: This review covers efforts toward the synthesis of Daphniphyllum alkaloids spanning the period from 2005 to the beginning of 2016, including reported biological activities as well as the isolation of new members of this genus.
Journal ArticleDOI
The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.
Artem Shvartsbart,Amos B. Smith +1 more
TL;DR: 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 one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselectives hydrogenation of a fully substituted diene ester.
Journal ArticleDOI
Strategies towards the synthesis of calyciphylline A-type Daphniphyllum alkaloids
TL;DR: A review of several noteworthy core syntheses and the development of a wide range of novel synthetic strategies have been achieved, including strategies based on intramolecular Michael addition, Pd-catalysis, cycloaddition, and Mannich-type reactions.
Journal ArticleDOI
Total Synthesis of (−)‐Daphenylline
TL;DR: Total synthesis of (-)-daphenylline, a hexacyclic Daphniphyllum alkaloid, was achieved and the ABC ring system was stereoselectively constructed through intramolecular cycloaddition of the cyclic azomethine ylide.
Journal ArticleDOI
Divergent Total Syntheses of (−)-Daphnilongeranin B and (−)-Daphenylline
Xiaoming Chen,Hai-Jun Zhang,Xinkan Yang,Houqiang Lv,Xiaoru Shao,Cheng Tao,Huifei Wang,Bin Cheng,Yun Li,Jing-Jing Guo,Jing Zhang,Hongbin Zhai,Hongbin Zhai +12 more
TL;DR: The key features include an intermolecular [3+2] cycloaddition, a late-stage aldol cyclization to install the F ring of daphnilongeranin B, and a bioinspired cationic rearrangement leading to the tetrasubstituted benzene ring of daphenylline.
References
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Journal ArticleDOI
Reduction of .DELTA.2-isoxazolines. 3. Raney nickel catalyzed formation of .beta.-hydroxy ketones
TL;DR: In this article, les conditions optimales de transformation d'isoxazolines-2 en β-hydroxycetones en utilisant un catalyseur Ni de Raney, l'acide borique, un melange 5/1 methanol/eau et l'hydrogene gazeux were determined.
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The Daphniphyllum alkaloids
TL;DR: This comprehensive review summarizes all the research into the isolation and structure elucidation of the Daphniphyllum alkaloids reported since investigations began in 1966.
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Total synthesis of the Daphniphyllum alkaloid daphenylline
TL;DR: This work describes the first total synthesis of daphenylline, a structurally unique member among the predominately aliphatic Daphniphyllum alkaloids, and contains a tetrasubstituted arene moiety mounted on a sterically compact hexacyclic scaffold.
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Stereocontrolled total synthesis of (+)-vinblastine.
Satoshi Yokoshima,Toshihiro Ueda,Satoshi Kobayashi,Ayato Sato,Takeshi Kuboyama,Hidetoshi Tokuyama,Tohru Fukuyama +6 more
TL;DR: A stereocontrolled total synthesis of (+)-vinblastine was accomplished, featuring preparations of the two indole units by means of a novel indole synthesis via radical cyclization of thioanilide, and a stereoselective coupling of these units.
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Total synthesis of (+)-daphmanidin E.
TL;DR: 9-16 1) 1.3-propanediol, pTsOH (10 mol%), PhH, reflux; then p TsOH ( 10 mol%), acetone, 50°C 2) KHMDS, 2-(NTf2)-pyridine, THF, -40°C 3) 1, 9-BBN, AsPh3 (16 mol%), [Pd2(dba)3]/CHCl3 (2 mol%), K