Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

2006 ◽  
Vol 128 (42) ◽  
pp. 13704-13705 ◽  
Author(s):  
Timothy J. Donohoe ◽  
Robert M. Harris ◽  
Jeremy Burrows ◽  
Jeremy Parker
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Cyclization Reactions

scholarly journals Total Synthesis of (+)-cis-Sylvaticin: Double Oxidative Cyclization Reactions Catalyzed by Osmium.

ChemInform ◽  
2007 ◽  
Vol 38 (11) ◽  
Author(s):  
Timothy J. Donohoe ◽  
Robert M. Harris ◽  
Jeremy Burrows ◽  
Jeremy Parker
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Cyclization Reactions

Oxidative Cyclization Reactions of Trienes and Dienynes: Total Synthesis of Membrarollin

2009 ◽  
Vol 74 (3) ◽  
pp. 981-988 ◽  
Author(s):  
Claire L. Morris ◽  
Yulai Hu ◽  
Geoff D. Head ◽  
Lynda J. Brown ◽  
William G. Whittingham ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Cyclization Reactions

scholarly journals Pt(II)-Decorated Covalent Organic Framework for Photocatalytic Difluoroalkylation and Oxidative Cyclization Reactions

2021 ◽  
Vol 13 (5) ◽  
pp. 6349-6358
Author(s):  
Zainab Almansaf ◽  
Jiyun Hu ◽  
Federica Zanca ◽  
Hamid R. Shahsavari ◽  
Benjamin Kampmeyer ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reactions ◽  
Covalent Organic Framework ◽  
Organic Framework

scholarly journals Oxidative cyclo-rearrangement of helicenes into chiral nanographenes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Chengshuo Shen ◽  
Guoli Zhang ◽  
Yongle Ding ◽  
Na Yang ◽  
Fuwei Gan ◽  
...  
Keyword(s):  
Functional Materials ◽  
Optical Devices ◽  
Oxidative Cyclization ◽  
Synthetic Chemistry ◽  
Aromatic Rings ◽  
Cyclization Reactions ◽  
Rearrangement Reaction ◽  
Skeletal Reconstruction ◽  
Gradual Release

AbstractNanographenes are emerging as a distinctive class of functional materials for electronic and optical devices. It is of remarkable significance to enrich the precise synthetic chemistry for these molecules. Herein, we develop a facile strategy to recompose helicenes into chiral nanographenes through a unique oxidative cyclo-rearrangement reaction. Helicenes with 7~9 ortho-fused aromatic rings are firstly oxidized and cyclized, and subsequently rearranged into nanographenes with an unsymmetrical helicoid shape through sequential 1,2-migrations. Such skeletal reconstruction is virtually driven by the gradual release of the strain of the highly distorted helicene skeleton. Importantly, the chirality of the helicene precursor can be integrally inherited by the resulting nanographene. Thus, a series of chiral nanographenes are prepared from a variety of carbohelicenes and heterohelicenes. Moreover, such cyclo-rearrangement reaction can be sequentially or simultaneously associated with conventional oxidative cyclization reactions to ulteriorly enrich the geometry diversity of nanographenes, aiming at innovative properties.

scholarly journals New cyclization reactions in organic syntheses

2002 ◽  
Vol 74 (1) ◽  
pp. 159-166 ◽  
Author(s):  
Iwao Ojima
Keyword(s):  
Amino Acids ◽  
Transition Metal ◽  
Total Synthesis ◽  
Cyclization Reactions ◽  
Organic Syntheses ◽  
Carbocyclic Compounds ◽  
Efficient Construction ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Recent development in the transition metal-catalyzed cyclization reactions for organic syntheses in the author's laboratories is summarized, which includes (i) novel silylcarbocyclizations (SiCaCs) and carbonylative carbotricyclizations, (ii) intramolecular silylformylations and desymmerization of siloxydiynes by sequential double silylformylation, (iii) efficient total synthesis of (+)-prosopinine, (iv) enantioselective desymmetrization of aminodienes, and (iv) new and efficient routes to 1-azabicyclo[x.y.0]alkane amino acids. All these processes are catalyzed by Rh or Rh­Co complexes, and useful for rapid and efficient construction of a variety of heterocyclic and carbocyclic compounds. Mechanisms of these new carbocyclization and cyclohydrocarbonylation reactions are also discussed.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

Intramolecular Michael Addition of N- and O-Centred Nucleophiles to Tethered Acrylates. The Role of Double-Bond Geometry in Controlling the Diastereo- selectivity of Cyclizations Leading to 2,6-Disubstituted Tetrahydropyrans and Piperidines.

1998 ◽  
Vol 51 (1) ◽  
pp. 9 ◽  
Author(s):  
Martin G. Banwell ◽  
Brett D. Bissett ◽  
Chinh T. Bui ◽  
Ha T. T. Pham ◽  
Gregory W. Simpson
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Michael Addition ◽  
Reductive Amination ◽  
Major Product ◽  
Enantioselective Synthesis ◽  
Cyclization Reactions ◽  
Glandular Secretion

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

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