Literature DB >> 27632643

Modular Terpenoid Construction via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Total Synthesis of Oridamycin A, Triptoquinones B and C, and Isoiresin.

Jiajie Feng1, Florian Noack1, Michael J Krische1.   

Abstract

Total syntheses of oridamycin A, triptoquinones B and C, and isoiresin are accomplished from a common intermediate prepared via iridium-catalyzed alcohol C-H tert-(hydroxy)prenylation - a byproduct-free process that forms an all-carbon quaternary stereocenter with excellent control of diastereo- and enantioselectivity.

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Year:  2016        PMID： 27632643      PMCID： PMC5096378          DOI： 10.1021/jacs.6b08902

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


  29 in total

Review 1.  A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors:  Ryan A Yoder; Jeffrey N Johnston
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

2.  Synthetic studies on (+)-ophiobolin A: asymmetric synthesis of the spirocyclic CD-ring moiety.

Authors:  Naoyoshi Noguchi; Masahisa Nakada
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

Review 3.  Structural biology and chemistry of the terpenoid cyclases.

Authors:  David W Christianson
Journal:  Chem Rev       Date:  2006-08       Impact factor: 60.622

4.  The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.

Authors:  Sherry R. Chemler; Dirk Trauner; Samuel J. Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

5.  Immunosuppressive diterpenoids from Tripterygium wilfordii.

Authors:  H Duan; Y Takaishi; H Momota; Y Ohmoto; T Taki; Y Jia; D Li
Journal:  J Nat Prod       Date:  1999-11       Impact factor: 4.050

6.  Terpene alkaloids from Tripterygium wilfordii.

Authors:  Xiao-Dong Wang; Wei Jia; Wen-Yuan Gao; Rong Zhang; Yan-Wen Zhang; Jun Zhang; Yoshihisa Takaishi; Hong-Quan Duan
Journal:  J Asian Nat Prod Res       Date:  2005-10       Impact factor: 1.569

7.  Air-stable trialkylphosphonium salts: simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes.

Authors:  M R Netherton; G C Fu
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

8.  First and second generation total synthesis of the teicoplanin aglycon.

Authors:  D L Boger; S H Kim; Y Mori; J H Weng; O Rogel; S L Castle; J J McAtee
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

9.  1H and 13C assignments of three new drimenes from Iresine diffusa Humb. & Bonpl. ex Willd.

Authors:  María Yolanda Rios; Laura Alvarez Berber
Journal:  Magn Reson Chem       Date:  2005-04       Impact factor: 2.447

10.  Kaurane and abietane diterpenoids from Tripterygium doianum (Celastraceae).

Authors:  Naonobu Tanaka; Nobuyuki Ooba; Hongquan Duan; Yoshihisa Takaishi; Yuka Nakanishi; Kenneth Bastow; Kuo-Hsiung Lee
Journal:  Phytochemistry       Date:  2004-07       Impact factor: 4.072
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  8 in total

1.  The High Chemofidelity of Metal-Catalyzed Hydrogen Atom Transfer.

Authors:  Samantha A Green; Steven W M Crossley; Jeishla L M Matos; Suhelen Vásquez-Céspedes; Sophia L Shevick; Ryan A Shenvi
Journal:  Acc Chem Res       Date:  2018-11-08       Impact factor: 22.384

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

4.  Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes.

Authors:  Yi-An Guo; Tao Liang; Seung Wook Kim; Hongde Xiao; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

Review 5.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

6.  Total Syntheses of Xiamycins A, C, F, H and Oridamycin A and Preliminary Evaluation of their Anti-Fungal Properties.

Authors:  Magnus Pfaffenbach; Ian Bakanas; Nicholas R O'Connor; Jessica L Herrick; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

7.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

8.  Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.

Authors:  Lin Yang; Thomas Wurm; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-15       Impact factor: 15.336
  8 in total

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