Literature DB >> 29417970

Total synthesis of complex terpenoids employing radical cascade processes.

Kevin Hung1, Xirui Hu, Thomas J Maimone.   

Abstract

Covering: 2011-2017Radical cyclizations have a rich history in organic chemistry and have been particularly generous to the field of natural product synthesis. Owing to their ability to operate in highly congested molecular quarters, and with significant functional group compatibility, these transformations have enabled the synthesis of numerous polycyclic terpenoid natural products over the past several decades. Moreover, when programmed accordingly into a synthetic plan, radical cascade processes can be used to rapidly assemble molecular complexity, much in the same way nature rapidly constructs terpene frameworks through cationic cyclization pathways. This review highlights recent total syntheses of complex terpenoids (from 2011-2017) employing C-C bond-forming radical cascade sequences.

Entities:  

Mesh:

Substances:

Year:  2018        PMID: 29417970      PMCID: PMC5858714          DOI: 10.1039/c7np00065k

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  131 in total

1.  Manganese(III)-Based Oxidative Free-Radical Cyclizations.

Authors:  Barry B. Snider
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Asymmetric Ni(II)/Cr(II)-mediated coupling reaction: stoichiometric process.

Authors:  Zhao-Kui Wan; Hyeong-Wook Choi; Fu-An Kang; Katsumasa Nakajima; Damtew Demeke; Yoshito Kishi
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  Total synthesis of (+)-pleuromutilin.

Authors:  Neal J Fazakerley; Matthew D Helm; David J Procter
Journal:  Chemistry       Date:  2013-04-15       Impact factor: 5.236

Review 5.  Diterpenoids from Isodon species: an update.

Authors:  Miao Liu; Wei-Guang Wang; Han-Dong Sun; Jian-Xin Pu
Journal:  Nat Prod Rep       Date:  2017-08-30       Impact factor: 13.423

6.  Total synthesis of (-)-jiadifenin.

Authors:  Yang Yang; Xingnian Fu; Jianwei Chen; Hongbin Zhai
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-24       Impact factor: 15.336

7.  A total synthesis of estrone based on a novel cascade of radical cyclizations.

Authors:  Gerald Pattenden; Miguel A Gonzalez; Stuart McCulloch; Affo Walter; Steven J Woodhead
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-10       Impact factor: 11.205

8.  Total synthesis of (+)-crotogoudin.

Authors:  Simon Breitler; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-26       Impact factor: 15.336

9.  Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors:  Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal:  Chemistry       Date:  2015-11-26       Impact factor: 5.236

10.  Photochemical Stereocontrol Using Tandem Photoredox-Chiral Lewis Acid Catalysis.

Authors:  Tehshik P Yoon
Journal:  Acc Chem Res       Date:  2016-08-09       Impact factor: 22.384

View more
  21 in total

1.  Photoexcitation of flavoenzymes enables a stereoselective radical cyclization.

Authors:  Kyle F Biegasiewicz; Simon J Cooper; Xin Gao; Daniel G Oblinsky; Ji Hye Kim; Samuel E Garfinkle; Leo A Joyce; Braddock A Sandoval; Gregory D Scholes; Todd K Hyster
Journal:  Science       Date:  2019-06-21       Impact factor: 47.728

2.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

3.  Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors:  Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal:  J Am Chem Soc       Date:  2019-01-04       Impact factor: 15.419

4.  Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

Authors:  Xirui Hu; Andrew J Musacchio; Xingyu Shen; Yujia Tao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

5.  Total Synthesis of (+)-6-epi-Ophiobolin A.

Authors:  Danny Q Thach; Zachary G Brill; Huck K Grover; Kenneth V Esguerra; Jordan K Thompson; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336

6.  Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species.

Authors:  Matthew L Condakes; Luiz F T Novaes; Thomas J Maimone
Journal:  J Org Chem       Date:  2018-12-07       Impact factor: 4.354

Review 7.  Syntheses of Complex Terpenes from Simple Polyprenyl Precursors.

Authors:  Claire S Harmange Magnani; Danny Q Thach; Karl T Haelsig; Thomas J Maimone
Journal:  Acc Chem Res       Date:  2020-03-23       Impact factor: 22.384

8.  Evolution of a Synthetic Strategy for Complex Polypyrrole Alkaloids: Total Syntheses of Curvulamine and Curindolizine.

Authors:  Jun Xuan; Karl T Haelsig; Michael Sheremet; Paulo A Machicao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2021-02-11       Impact factor: 15.419

9.  Three-component three-bond forming cascade via palladium photoredox catalysis.

Authors:  Peter Bellotti; Maximilian Koy; Christian Gutheil; Steffen Heuvel; Frank Glorius
Journal:  Chem Sci       Date:  2020-12-07       Impact factor: 9.825

Review 10.  Activation modes in biocatalytic radical cyclization reactions.

Authors:  Yuxuan Ye; Haigen Fu; Todd K Hyster
Journal:  J Ind Microbiol Biotechnol       Date:  2021-06-04       Impact factor: 4.258

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.