Literature DB >> 22449198

Total synthesis of (±)-7-epi-nemorosone.

Qiang Zhang1, John A Porco.   

Abstract

A concise total synthesis of (±)-7-epi-nemorosone is reported. Our synthetic approach establishes a viable route to polycyclic polyprenylated acylphloroglucinol natural products (PPAP's) bearing a C-7 endo prenyl side chain. Key steps include retro-aldol-vinyl cerium addition to a hydroxy adamantane core scaffold and palladium-mediated deoxygenation.

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Year:  2012        PMID： 22449198      PMCID： PMC3326386          DOI： 10.1021/ol300386t

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


  25 in total

1.  Floral resin of Tovomitopsis saldanhae (Guttiferae) and 7-epi-nemorosone: structural revision.

Authors:  Volker Bittrich; Maria do Carmo E Amaral; Samísia M F Machado; Anita J Marsaioli
Journal:  Z Naturforsch C J Biosci       Date:  2003 Sep-Oct

2.  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

3.  Catalytic asymmetric total synthesis of ent-hyperforin.

Authors:  Yohei Shimizu; Shi-Liang Shi; Hiroyuki Usuda; Motomu Kanai; Masakatsu Shibasaki
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-01       Impact factor: 15.336

4.  Total synthesis of (+/-)-garsubellin A.

Authors:  Akiyoshi Kuramochi; Hiroyuki Usuda; Kenzo Yamatsugu; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

5.  The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

Authors:  Nicole Biber; Katrin Möws; Bernd Plietker
Journal:  Nat Chem       Date:  2011-10-16       Impact factor: 24.427

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.  Synthesis of (+/-)-clusianone: high-yielding bridgehead and diketone substitutions by regioselective lithiation of enol ether derivatives of bicyclo[3.3.1]nonane-2,4,9-triones.

Authors:  Vincent Rodeschini; Nadia M Ahmad; Nigel S Simpkins
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

8.  The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.

Authors:  David Díaz-Carballo; Sascha Malak; Walter Bardenheuer; Michael Freistuehler; H Peter Reusch
Journal:  Bioorg Med Chem       Date:  2008-10-11       Impact factor: 3.641

9.  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

10.  Polyisoprenylated benzophenones in cuban propolis; biological activity of nemorosone.

Authors:  Osmany Cuesta-Rubio; Bernardo A Frontana-Uribe; Teresa Ramírez-Apan; Jorge Cárdenas
Journal:  Z Naturforsch C J Biosci       Date:  2002 Mar-Apr
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  9 in total

1.  Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors:  Mikayo Hayashi; Lauren E Brown; John A Porco
Journal:  European J Org Chem       Date:  2016-10

2.  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

3.  Evolution of an oxidative dearomatization enabled total synthesis of vinigrol.

Authors:  Qingliang Yang; Cristian Draghici; Jon T Njardarson; Fang Li; Brandon R Smith; Pradipta Das
Journal:  Org Biomol Chem       Date:  2014-01-14       Impact factor: 3.876

4.  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

Review 5.  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

6.  Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Authors:  Alexander J Grenning; Jonathan H Boyce; John A Porco
Journal:  J Am Chem Soc       Date:  2014-08-07       Impact factor: 15.419

7.  Identification of a novel polyprenylated acylphloroglucinol‑derived SIRT1 inhibitor with cancer‑specific anti-proliferative and invasion-suppressing activities.

Authors:  Lijia Zhu; Ji Qi; Christine Ya-Chi Chiao; Qiang Zhang; John A Porco; Douglas V Faller; Yan Dai
Journal:  Int J Oncol       Date:  2014-09-03       Impact factor: 5.650

8.  Programmable meroterpene synthesis.

Authors:  Xingyu Shen; Chi P Ting; Gong Xu; Thomas J Maimone
Journal:  Nat Commun       Date:  2020-01-24       Impact factor: 14.919

9.  Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.

Authors:  Jonathan H Boyce; Benjamin J Reisman; Brian O Bachmann; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336
  9 in total

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