Literature DB >> 16898786

Approach to the synthesis of cladiell-11-ene-3,6,7-triol.

John M Hutchison1, Harriet A Lindsay, Silvana S Dormi, Gavin D Jones, David A Vicic, Matthias C McIntosh.   

Abstract

[reaction: see text] The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland-Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an SN2' reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.

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Year:  2006        PMID： 16898786     DOI： 10.1021/ol061072j

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


  9 in total

1.  Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.

Authors:  Aaron T Herrmann; Tatsuo Saito; Craig E Stivala; Janine Tom; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

2.  Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis-Spiroketal Synthesis.

Authors:  Austin H Asari; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-25       Impact factor: 15.336

3.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

4.  The catalytic asymmetric Diels-Alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes.

Authors:  Hao Xie; Glenn M Sammis; Eric M Flamme; Christina M Kraml; Erik J Sorensen
Journal:  Chemistry       Date:  2011-09-05       Impact factor: 5.236

5.  Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.

Authors:  Yao Jiang; Regan J Thomson; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-04       Impact factor: 15.336

6.  Acyclic 1,4-stereocontrol via reductive 1,3-transpositions.

Authors:  Wei Qi; Matthias C McIntosh
Journal:  Org Lett       Date:  2007-12-20       Impact factor: 6.005

7.  Total synthesis of phomactin A.

Authors:  Yu Tang; Kevin P Cole; Grant S Buchanan; Gang Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

8.  Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

Authors:  T David Bateman; Aarti L Joshi; Kwangyul Moon; Elena N Galitovskaya; Meenakshi Upreti; Timothy C Chambers; Matthias C McIntosh
Journal:  Bioorg Med Chem Lett       Date:  2009-10-22       Impact factor: 2.823

9.  Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.

Authors:  Youwei Xie; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336
  9 in total

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