Literature DB >> 28514145

Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C.

Yuriy Slutskyy1, Christopher R Jamison1, Peng Zhao1, Juyeol Lee1, Young Ho Rhee2, Larry E Overman1.   

Abstract

A short enantioselective synthesis of 6-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-ones is described. The pivotal step is coupling of a tertiary radical generated directly from a tertiary alcohol with a 3-chloro-5-alkoxybutenolide. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids: cheloviolenes A and B and dendrillolide C.

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Year:  2017        PMID： 28514145     DOI： 10.1021/jacs.7b04265

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


  9 in total

1.  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

2.  Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.

Authors:  Xinpei Cai; Weida Liang; Mingxin Liu; Xiating Li; Mingji Dai
Journal:  J Am Chem Soc       Date:  2020-07-27       Impact factor: 15.419

3.  Radicals in natural product synthesis.

Authors:  Kevin J Romero; Matthew S Galliher; Derek A Pratt; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2018-10-29       Impact factor: 54.564

4.  Photocatalytic reverse polarity Povarov reaction.

Authors:  Jamie A Leitch; Angel L Fuentes de Arriba; Joanne Tan; Oskar Hoff; Carlos M Martínez; Darren J Dixon
Journal:  Chem Sci       Date:  2018-07-06       Impact factor: 9.825

5.  Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.

Authors:  Francisco José Aguilar Troyano; Frederic Ballaschk; Marcel Jaschinski; Yasemin Özkaya; Adrián Gómez-Suárez
Journal:  Chemistry       Date:  2019-10-18       Impact factor: 5.236

Review 6.  Catalytic Asymmetric Hydroalkoxylation of C-C Multiple Bonds.

Authors:  Jennifer L Kennemur; Rajat Maji; Manuel J Scharf; Benjamin List
Journal:  Chem Rev       Date:  2021-12-03       Impact factor: 60.622

7.  Efficient and practical synthesis of monoalkyl oxalates under green conditions.

Authors:  Tatiana Barsukova; Takeyuki Sato; Haruki Takumi; Satomi Niwayama
Journal:  RSC Adv       Date:  2022-09-12       Impact factor: 4.036

8.  Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo[3.3.0]octanone Fragment.

Authors:  Tyler K Allred; André P Dieskau; Peng Zhao; Gregory L Lackner; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-19       Impact factor: 15.336

9.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622
  9 in total

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