Literature DB >> 29897247

An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol.

Chen Xu1,2, Arthur Han2, Sarah E Reisman2.   

Abstract

An approach to synthesize the pentacyclic framework of the polyol diterpenoid ryanodol is reported. The ABC tricycle was constructed by a Co-mediated Pauson-Khand reaction, and both radical and anionic cyclization pathways were developed to form the E-ring. In addition, a reaction sequence involving SeO2-mediated enone oxidation and hydroxyl-directed oxy-Michael addition was developed to introduce the A-ring oxidation. The feasibility of forming the bridging D-ring by an oxidative dearomatization was established.

Entities:  

Year:  2018        PMID： 29897247      PMCID： PMC6103443          DOI： 10.1021/acs.orglett.8b01387

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


  20 in total

1.  Plant insecticides; ryanodine, a new alkaloid from Ryania speciosa Vahl.

Authors:  E F ROGERS; F R KONIUSZY
Journal:  J Am Chem Soc       Date:  1948-09       Impact factor: 15.419

Review 2.  The pharmacology of ryanodine and related compounds.

Authors:  J L Sutko; J A Airey; W Welch; L Ruest
Journal:  Pharmacol Rev       Date:  1997-03       Impact factor: 25.468

3.  Minor diterpenes from Persea indica: their antifeedant activity.

Authors:  B M Fraga; D Terrero; C Gutiérrez; A González-Coloma
Journal:  Phytochemistry       Date:  2001-02       Impact factor: 4.072

4.  Pd(PhCN)(2)Cl(2)/P(t-Bu)(3): a versatile catalyst for Sonogashira reactions of aryl bromides at room temperature.

Authors:  T Hundertmark; A F Littke; S L Buchwald; G C Fu
Journal:  Org Lett       Date:  2000-06-15       Impact factor: 6.005

5.  Minor constituents of Spigelia anthelmia and their cardiac activities.

Authors:  H Hübner; W Vierling; W Brandt; M Reiter; H Achenbach
Journal:  Phytochemistry       Date:  2001-05       Impact factor: 4.072

6.  A 15-step synthesis of (+)-ryanodol.

Authors:  Kangway V Chuang; Chen Xu; Sarah E Reisman
Journal:  Science       Date:  2016-08-26       Impact factor: 47.728

7.  Isolation of the ryanodine receptor from cardiac sarcoplasmic reticulum and identity with the feet structures.

Authors:  M Inui; A Saito; S Fleischer
Journal:  J Biol Chem       Date:  1987-11-15       Impact factor: 5.157

8.  Enantioselective, organocatalytic oxy-michael addition to gamma/delta-hydroxy-alpha,beta-enones: boronate-amine complexes as chiral hydroxide synthons.

Authors:  De Run Li; Andiappan Murugan; J R Falck
Journal:  J Am Chem Soc       Date:  2007-12-13       Impact factor: 15.419

9.  The calcium-ryanodine receptor complex of skeletal and cardiac muscle.

Authors:  I N Pessah; A L Waterhouse; J E Casida
Journal:  Biochem Biophys Res Commun       Date:  1985-04-16       Impact factor: 3.575

10.  Total synthesis of ryanodol.

Authors:  Masanori Nagatomo; Masaki Koshimizu; Kengo Masuda; Toshiki Tabuchi; Daisuke Urabe; Masayuki Inoue
Journal:  J Am Chem Soc       Date:  2014-04-11       Impact factor: 15.419
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  2 in total

1.  Synthesis of Complex Diterpenes: Strategies Guided by Oxidation Pattern Analysis.

Authors:  Sara E Dibrell; Yujia Tao; Sarah E Reisman
Journal:  Acc Chem Res       Date:  2021-02-23       Impact factor: 24.466

Review 2.  High-Productivity Single-Pass Electrochemical Birch Reduction of Naphthalenes in a Continuous Flow Electrochemical Taylor Vortex Reactor.

Authors:  Darren S Lee; Ashley Love; Zakaria Mansouri; Toby H Waldron Clarke; David C Harrowven; Richard Jefferson-Loveday; Stephen J Pickering; Martyn Poliakoff; Michael W George
Journal:  Org Process Res Dev       Date:  2022-08-24       Impact factor: 3.858
  2 in total

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