Literature DB >> 12952441

Total synthesis of merrilactone A.

Masayuki Inoue1, Takaaki Sato, Masahiro Hirama.   

Abstract

Merrilactone A (1) has been shown to possess neurotrophic activity and thus is expected to hold therapeutic potential in the treatment of neurodegeneration diseases. In this paper, we report the total synthesis of (+/-)-1, employing, as key steps, a novel desymmetrization protocol of meso-diketone to construct the core cis-bicyclo[3.3.0]octyl system of 1 (3 --> 2) and a radical cyclization to install the highly congested C9-quaternary carbon (16 --> 17).

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Year:  2003        PMID： 12952441     DOI： 10.1021/ja036587+

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 in total

Review 1.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

2.  Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors:  Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-02-11       Impact factor: 15.419

3.  A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

4.  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

5.  Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.

Authors:  Xiayun Cheng; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2016-01-25       Impact factor: 15.419

6.  Construction of bicyclic ring systems via a transannular SmI2-mediated ketone-olefin cyclization strategy.

Authors:  Gary A Molander; Barbara Czakó; Michael Rheam
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

7.  Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

Authors:  Kevin Hung; Matthew L Condakes; Takahiro Morikawa; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2016-12-16       Impact factor: 15.419

8.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2013-03-22       Impact factor: 5.236

9.  Substituent effects on the rearrangements of cyclohexyl to cyclopentyl radicals involving avermectin-related radicals.

Authors:  Jennifer A R Luft; Tammo Winkler; Fiona M Kessabi; K N Houk
Journal:  J Org Chem       Date:  2008-10-09       Impact factor: 4.354

Review 10.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622
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