Literature DB >> 24525557

Synthetic strategies toward hetidine and hetisine-type diterpenoid alkaloids.

Amy M Hamlin1, Jessica K Kisunzu, Richmond Sarpong.   

Abstract

Within the diterpenoid alkaloid family of natural products, the hetidine and hetisine structural types have been the targets of a number of synthetic studies. Various strategies have been pursued to access the azacyclic moiety of these natural products as well as the characteristic [2.2.2] bicyclic structural motif. This perspective article examines the different disconnections and approaches that have been applied to the synthesis of these natural products to date.

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Year:  2014        PMID: 24525557     DOI: 10.1039/c3ob42541j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  8 in total

1.  A three-component coupling approach to the ACE-ring substructure of C19-diterpene alkaloids.

Authors:  Kosuke Minagawa; Daisuke Urabe; Masayuki Inoue
Journal:  J Antibiot (Tokyo)       Date:  2017-06-14       Impact factor: 2.649

2.  A Benzyne Insertion Approach to Hetisine-Type Diterpenoid Alkaloids: Synthesis of Cossonidine (Davisine).

Authors:  Kevin G M Kou; Jason J Pflueger; Toshihiro Kiho; Louis C Morrill; Ethan L Fisher; Kyle Clagg; Terry P Lebold; Jessica K Kisunzu; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2018-06-19       Impact factor: 15.419

3.  A unified approach to ent-atisane diterpenes and related alkaloids: synthesis of (-)-methyl atisenoate, (-)-isoatisine, and the hetidine skeleton.

Authors:  Emily C Cherney; Justin M Lopchuk; Jason C Green; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-08-29       Impact factor: 15.419

4.  Total synthesis of avenaol.

Authors:  Motohiro Yasui; Rina Ota; Chihiro Tsukano; Yoshiji Takemoto
Journal:  Nat Commun       Date:  2017-09-22       Impact factor: 14.919

Review 5.  A Case for Bond-Network Analysis in the Synthesis of Bridged Polycyclic Complex Molecules: Hetidine and Hetisine Diterpenoid Alkaloids.

Authors:  Nicolle A Doering; Richmond Sarpong; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-15       Impact factor: 15.336

6.  Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process.

Authors:  Koichi Hagiwara; Toshiki Tabuchi; Daisuke Urabe; Masayuki Inoue
Journal:  Chem Sci       Date:  2016-03-18       Impact factor: 9.825

7.  Studies on C20-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton.

Authors:  Amy M Hamlin; David Lapointe; Kyle Owens; Richmond Sarpong
Journal:  J Org Chem       Date:  2014-07-11       Impact factor: 4.354

8.  Total synthesis of atropurpuran.

Authors:  Jing Gong; Huan Chen; Xiao-Yu Liu; Zhi-Xiu Wang; Wei Nie; Yong Qin
Journal:  Nat Commun       Date:  2016-07-08       Impact factor: 14.919

  8 in total

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