Literature DB >> 21162546

Synthesis of the cyclohexane core of phomactins and a new route to the bicyclo[9.3.1]pentadecane diterpenoid skeleton.

Keith D Schwartz1, James D White.   

Abstract

Conjugate reduction of an enone accompanied by in situ intramolecular aldol condensation was used to construct the tetrasubstituted cyclohexane nucleus of phomactins. Subsequent relay ring-closing metathesis completed the nine-membered ansa bridge of the diterpenoid framework.

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Year:  2010        PMID： 21162546     DOI： 10.1021/ol1026816

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


  7 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.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

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.  C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.

Authors:  Paul R Leger; Yusuke Kuroda; Stanley Chang; Justin Jurczyk; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2020-08-31       Impact factor: 15.419

7.  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
  7 in total

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