Literature DB >> 19736911

Beta-iodoallenolates as springboards for annulation reactions.

Jennifer Ciesielski1, Daniel P Canterbury, Alison J Frontier.   

Abstract

Beta-iodoallenolates II, generated from alkynones I with tetra-n-butylammonium iodide and a Lewis acid, underwent selective single or double annulation, depending on the Lewis acid promoter. Treatment with TiCl(4) gave cyclohexenyl alcohols III, whereas BF(3) x OEt(2) gave oxadecalins IV. The scope and limitations of the two annulation reactions are described.

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Year:  2009        PMID： 19736911     DOI： 10.1021/ol901721y

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


  6 in total

1.  Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors:  Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal:  J Org Chem       Date:  2011-08-05       Impact factor: 4.354

2.  Total synthesis and absolute stereochemical assignment of kibdelone C.

Authors:  David L Sloman; Jeffrey W Bacon; John A Porco
Journal:  J Am Chem Soc       Date:  2011-06-15       Impact factor: 15.419

3.  Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

Authors:  Jennifer Ciesielski; Vincent Gandon; Alison J Frontier
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

4.  Gold (III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

Authors:  Jennifer Ciesielski; David Lebœuf; Harry A Stern; Alison J Frontier
Journal:  Adv Synth Catal       Date:  2013-07-08       Impact factor: 5.837

5.  Constructing the Architecturally Distinctive ABD-Tricycle of Phomactin A through an Intramolecular Oxa-[3 + 3] Annulation Strategy.

Authors:  Grant S Buchanan; Kevin P Cole; Gang Li; Yu Tang; Ling-Feng You; Richard P Hsung
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

6.  A macrocyclic β-iodoallenolate intermediate is key: synthesis of the ABD core of phomactin A.

Authors:  Jennifer Ciesielski; Kevin Cariou; Alison J Frontier
Journal:  Org Lett       Date:  2012-08-02       Impact factor: 6.005
  6 in total

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