Literature DB >> 26186274

Total Synthesis of Aquatolide.

Jordy M Saya1, Klaas Vos1, Roel A Kleinnijenhuis1, Jan H van Maarseveen1, Steen Ingemann1, Henk Hiemstra1.   

Abstract

A total synthesis of the sesquiterpene lactone aquatolide has been accomplished. The central step is an intramolecular [2 + 2]-photocycloaddition of an allene onto an α,β-unsaturated δ-lactone. Other key steps are an intramolecular Horner-Wadsworth-Emmons reaction to close the lactone and an intramolecular Mukaiyama-type aldol reaction to cyclize the eight-membered ring. Racemic aquatolide has been resolved using preparative HPLC.

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Year:  2015        PMID： 26186274     DOI： 10.1021/acs.orglett.5b01888

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

2.  Unequivocal determination of complex molecular structures using anisotropic NMR measurements.

Authors:  Yizhou Liu; Josep Saurí; Emily Mevers; Mark W Peczuh; Henk Hiemstra; Jon Clardy; Gary E Martin; R Thomas Williamson
Journal:  Science       Date:  2017-04-07       Impact factor: 47.728

3.  Questions in natural products synthesis research that can (and cannot) be answered using computational chemistry.

Authors:  Dean J Tantillo
Journal:  Chem Soc Rev       Date:  2018-10-29       Impact factor: 54.564

4.  Dissemination of original NMR data enhances reproducibility and integrity in chemical research.

Authors:  Jonathan Bisson; Charlotte Simmler; Shao-Nong Chen; J Brent Friesen; David C Lankin; James B McAlpine; Guido F Pauli
Journal:  Nat Prod Rep       Date:  2016-08-25       Impact factor: 13.423

Review 5.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

6.  Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.

Authors:  Jian-Siang Poh; Szabolcs Makai; Timo von Keutz; Duc N Tran; Claudio Battilocchio; Patrick Pasau; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-11       Impact factor: 15.336

7.  Enantioselective crossed intramolecular [2+2] photocycloaddition reactions mediated by a chiral chelating Lewis acid.

Authors:  Thomas Rigotti; Daniel P Schwinger; Raphaela Graßl; Christian Jandl; Thorsten Bach
Journal:  Chem Sci       Date:  2022-02-01       Impact factor: 9.825

Review 8.  The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

Authors:  James B McAlpine; Shao-Nong Chen; Andrei Kutateladze; John B MacMillan; Giovanni Appendino; Andersson Barison; Mehdi A Beniddir; Maique W Biavatti; Stefan Bluml; Asmaa Boufridi; Mark S Butler; Robert J Capon; Young H Choi; David Coppage; Phillip Crews; Michael T Crimmins; Marie Csete; Pradeep Dewapriya; Joseph M Egan; Mary J Garson; Grégory Genta-Jouve; William H Gerwick; Harald Gross; Mary Kay Harper; Precilia Hermanto; James M Hook; Luke Hunter; Damien Jeannerat; Nai-Yun Ji; Tyler A Johnson; David G I Kingston; Hiroyuki Koshino; Hsiau-Wei Lee; Guy Lewin; Jie Li; Roger G Linington; Miaomiao Liu; Kerry L McPhail; Tadeusz F Molinski; Bradley S Moore; Joo-Won Nam; Ram P Neupane; Matthias Niemitz; Jean-Marc Nuzillard; Nicholas H Oberlies; Fernanda M M Ocampos; Guohui Pan; Ronald J Quinn; D Sai Reddy; Jean-Hugues Renault; José Rivera-Chávez; Wolfgang Robien; Carla M Saunders; Thomas J Schmidt; Christoph Seger; Ben Shen; Christoph Steinbeck; Hermann Stuppner; Sonja Sturm; Orazio Taglialatela-Scafati; Dean J Tantillo; Robert Verpoorte; Bin-Gui Wang; Craig M Williams; Philip G Williams; Julien Wist; Jian-Min Yue; Chen Zhang; Zhengren Xu; Charlotte Simmler; David C Lankin; Jonathan Bisson; Guido F Pauli
Journal:  Nat Prod Rep       Date:  2018-07-13       Impact factor: 13.423

9.  Toward Structural Correctness: Aquatolide and the Importance of 1D Proton NMR FID Archiving.

Authors:  Guido F Pauli; Matthias Niemitz; Jonathan Bisson; Michael W Lodewyk; Cristian Soldi; Jared T Shaw; Dean J Tantillo; Jordy M Saya; Klaas Vos; Roel A Kleinnijenhuis; Henk Hiemstra; Shao-Nong Chen; James B McAlpine; David C Lankin; J Brent Friesen
Journal:  J Org Chem       Date:  2016-01-26       Impact factor: 4.354

Review 10.  Computational Methodologies in the Exploration of Marine Natural Product Leads.

Authors:  Florbela Pereira; Joao Aires-de-Sousa
Journal:  Mar Drugs       Date:  2018-07-13       Impact factor: 5.118
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