Literature DB >> 29360385

Enantioselective, Protecting-Group-Free Total Synthesis of Boscartin F.

Akinobu Matsuzawa1, Junya Shiraiwa1, Akihiko Kasamatsu1, Kazuyuki Sugita1.   

Abstract

In this work, the protecting-group-free total synthesis and stereochemical assignment of (-)-boscartin F have been reported. The key steps, including Sharpless asymmetric epoxidation, I2-mediated iodoetherification, aldol reaction, and ring-closing metathesis, allowed for rapid and highly stereoselective access to boscartin F. In addition, single-crystal X-ray crystallographic analysis of the semicarbazone derivative 22 confirmed the stereochemistry of boscartin F.

Entities:  

Year:  2018        PMID: 29360385     DOI: 10.1021/acs.orglett.7b03979

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


  2 in total

1.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

2.  E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing.

Authors:  Yucheng Mu; Felix W W Hartrampf; Elsie C Yu; Katherine E Lounsbury; Richard R Schrock; Filippo Romiti; Amir H Hoveyda
Journal:  Nat Chem       Date:  2022-05-16       Impact factor: 24.274

  2 in total

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