Literature DB >> 11463290

Toward the total synthesis of variecolin.

G A Molander1, M S Quirmbach, L F Silva, K C Spencer, J Balsells.   

Abstract

[reaction: see text] An annulative approach toward the total synthesis of the sesterterpenoid variecolin (1) is presented. Synthesis of the key hemiketal, containing the core ABC ring skeleton, has been achieved on a model system by an expeditious route utilizing samarium(II) iodide. Furthermore, enantioselective syntheses of component fragments for the total synthesis have been developed.

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Year:  2001        PMID： 11463290     DOI： 10.1021/ol015763l

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


  6 in total

1.  Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin.

Authors:  Michael R Krout; Christopher E Henry; Thomas Jensen; Kun-Liang Wu; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2018-01-23       Impact factor: 4.354

Review 2.  Samarium diiodide mediated reactions in total synthesis.

Authors:  K C Nicolaou; Shelby P Ellery; Jason S Chen
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin.

Authors:  Daniel T Hog; Florian M E Huber; Gonzalo Jiménez-Osés; Peter Mayer; Kendall N Houk; Dirk Trauner
Journal:  Chemistry       Date:  2015-08-20       Impact factor: 5.236

4.  Isolation and structure elucidation of three new dolastanes from the brown alga Dilophus spiralis.

Authors:  Efstathia Ioannou; Constantinos Vagias; Vassilios Roussis
Journal:  Mar Drugs       Date:  2013-04-02       Impact factor: 5.118

5.  A scalable platform to identify fungal secondary metabolites and their gene clusters.

Authors:  Kenneth D Clevenger; Jin Woo Bok; Rosa Ye; Galen P Miley; Maria H Verdan; Thomas Velk; Cynthia Chen; KaHoua Yang; Matthew T Robey; Peng Gao; Matthew Lamprecht; Paul M Thomas; Md Nurul Islam; Jonathan M Palmer; Chengcang C Wu; Nancy P Keller; Neil L Kelleher
Journal:  Nat Chem Biol       Date:  2017-06-12       Impact factor: 15.040

6.  Preparation and use of samarium diiodide (SmI(2)) in organic synthesis: the mechanistic role of HMPA and Ni(II) salts in the samarium Barbier reaction.

Authors:  Dhandapani V Sadasivam; Kimberly A Choquette; Robert A Flowers
Journal:  J Vis Exp       Date:  2013-02-04       Impact factor: 1.355
  6 in total

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