Literature DB >> 11382245

Nemorosone, the major constituent of floral resins of Clusia rosea.

O Cuesta-Rubio1, H Velez-Castro, B A Frontana-Uribe, J Cardenas.   

Abstract

Nemorosone, the major constituent of the floral resin of Clusia rosea was isolated after exhaustive chromatography. This compound was fully characterized as it is in the nature, without methylation as reported before. A keto-enol equilibrium was observed and both isomers were totally characterized by NMR spectroscopic techniques. The previously announced structure for methylnemorosone was corrected on the basis of application of chemical methylation, high field 2D NMR techniques and NOE difference spectroscopy experiments on the natural product. Our studies concluded that an interchange occurred in the assignment of the benzoyl moiety position with an isoprenyl group in that structure.

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Year:  2001        PMID: 11382245     DOI: 10.1016/s0031-9422(00)00510-0

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  15 in total

1.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

2.  Microarray analysis of nemorosone-induced cytotoxic effects on pancreatic cancer cells reveals activation of the unfolded protein response (UPR).

Authors:  Frank Holtrup; Andrea Bauer; Kurt Fellenberg; Ralf A Hilger; Michael Wink; Jörg D Hoheisel
Journal:  Br J Pharmacol       Date:  2011-03       Impact factor: 8.739

3.  Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors:  Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

4.  Progress towards the synthesis of Papuaforin A: Selective formation of α-bromoenones from silyl enol ethers.

Authors:  George A Kraus; Insik Jeon
Journal:  Tetrahedron Lett       Date:  2008-01-07       Impact factor: 2.415

5.  Cytotoxic polyisoprenyl benzophenonoids from Garcinia subelliptica.

Authors:  Li-Jie Zhang; Chun-Tang Chiou; Jing-Jy Cheng; Hui-Chi Huang; Li-Ming Yang Kuo; Chia-Chin Liao; Kenneth F Bastow; Kuo-Hsiung Lee; Yao-Haur Kuo
Journal:  J Nat Prod       Date:  2010-04-23       Impact factor: 4.050

6.  Total synthesis of plukenetione A.

Authors:  Qiang Zhang; Branko Mitasev; Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Authors:  Jonathan H Boyce; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

8.  Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

Authors:  Jon T Njardarson
Journal:  Tetrahedron       Date:  2011-10-07       Impact factor: 2.457

9.  Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry.

Authors:  Anna Lisa Piccinelli; Luca Campone; Fabrizio Dal Piaz; Osmany Cuesta-Rubio; Luca Rastrelli
Journal:  J Am Soc Mass Spectrom       Date:  2009-05-20       Impact factor: 3.109

10.  Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.

Authors:  Branko Mitasev; John A Porco
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

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