Literature DB >> 22946620

Total synthesis of (+)-aureol.

Kevin K W Kuan1, Henry P Pepper, Witold M Bloch, Jonathan H George.   

Abstract

A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimetic cycloetherification reaction.

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Year:  2012        PMID: 22946620     DOI: 10.1021/ol301715u

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


  9 in total

Review 1.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

Review 2.  The chemistry of isoindole natural products.

Authors:  Klaus Speck; Thomas Magauer
Journal:  Beilstein J Org Chem       Date:  2013-10-10       Impact factor: 2.883

3.  Bioactive marine drugs and marine biomaterials for brain diseases.

Authors:  Clara Grosso; Patrícia Valentão; Federico Ferreres; Paula B Andrade
Journal:  Mar Drugs       Date:  2014-05-02       Impact factor: 5.118

4.  A modular synthesis of tetracyclic meroterpenoid antibiotics.

Authors:  Raphael Wildermuth; Klaus Speck; Franz-Lucas Haut; Peter Mayer; Bianka Karge; Mark Brönstrup; Thomas Magauer
Journal:  Nat Commun       Date:  2017-12-12       Impact factor: 14.919

Review 5.  Cytotoxic Compounds Derived from Marine Sponges. A Review (2010-2012).

Authors:  Roberto Mioso; Francisco J Toledo Marante; Ranilson de Souza Bezerra; Flávio Valadares Pereira Borges; Bárbara V de Oliveira Santos; Irma Herrera Bravo de Laguna
Journal:  Molecules       Date:  2017-01-28       Impact factor: 4.411

Review 6.  Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin .

Authors:  Pablo A García; Ángela P Hernández; Arturo San Feliciano; Mª Ángeles Castro
Journal:  Mar Drugs       Date:  2018-08-21       Impact factor: 5.118

Review 7.  Divergent Strategy in Marine Tetracyclic Meroterpenoids Synthesis.

Authors:  Antonio Rosales Martínez; Ignacio Rodríguez-García; Josefa L López-Martínez
Journal:  Mar Drugs       Date:  2021-05-13       Impact factor: 5.118

8.  Bioinspired synthesis of pentacyclic onocerane triterpenoids.

Authors:  Florian Bartels; Young J Hong; Daijiro Ueda; Manuela Weber; Tsutomu Sato; Dean J Tantillo; Mathias Christmann
Journal:  Chem Sci       Date:  2017-10-16       Impact factor: 9.825

9.  A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation.

Authors:  Antonio Rosales Martínez; Lourdes Enríquez; Martín Jaraíz; Laura Pozo Morales; Ignacio Rodríguez-García; Emilio Díaz Ojeda
Journal:  Mar Drugs       Date:  2020-08-26       Impact factor: 5.118

  9 in total

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