Literature DB >> 25591135

Synthesis of (±)-aureol by bioinspired rearrangements.

Antonio Rosales1, Juan Muñoz-Bascón, Esther Roldan-Molina, Nazaret Rivas-Bascón, Natalia M Padial, Roman Rodríguez-Maecker, Ignacio Rodríguez-García, J Enrique Oltra.   

Abstract

A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired sequence of 1,2-hydride and methyl shifts.

Entities:  

Mesh:

Substances:

Year:  2015        PMID: 25591135     DOI: 10.1021/jo502841u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 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

2.  Enantioselective Total Synthesis and Structural Revision of Dysiherbol A.

Authors:  Julian Baars; Isabelle Grimm; Dirk Blunk; Jörg-Martin Neudörfl; Hans-Günther Schmalz
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-01       Impact factor: 15.336

3.  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 4.  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 5.  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

6.  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

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.