Literature DB >> 14664384

A total synthesis of (+/-)-phomactin A.

Christopher M Diaper1, William P D Goldring, Gerald Pattenden.   

Abstract

A total synthesis of the PAF antagonist phomactin A (1), isolated from the marine fungus Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 14, leading to the key phomactatrienol intermediate 16a, followed by elaboration of 16a to the epoxyketone 21, which undergoes spontaneous pyran and hemiacetal ring formation to 1 on deprotection with DDQ.

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Year:  2003        PMID： 14664384     DOI： 10.1039/b307986d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  9 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.  An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors:  Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal:  Adv Synth Catal       Date:  2008-12-18       Impact factor: 5.837

3.  Studies toward the synthesis of phomactin A. An approach to the macrocyclic core.

Authors:  Dawei Teng; Bo Wang; Alex J Augatis; Nancy I Totah
Journal:  Tetrahedron Lett       Date:  2007-06-25       Impact factor: 2.415

4.  Total synthesis of (+/-)-phomactin B2 via an intramolecular cyclohexadienone annulation of a chromium carbene complex.

Authors:  Jie Huang; Chunrui Wu; William D Wulff
Journal:  J Am Chem Soc       Date:  2007-10-12       Impact factor: 15.419

5.  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

6.  Intramolecular cyclohexadienone annulations of Fischer carbene complexes: model studies for the synthesis of Phomactins.

Authors:  Jie Huang; Huan Wang; Chunrui Wu; William D Wulff
Journal:  Org Lett       Date:  2007-06-20       Impact factor: 6.005

7.  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

8.  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

9.  An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors:  Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal:  Adv Synth Catal       Date:  2008-12-01       Impact factor: 5.837
  9 in total

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