Literature DB >> 18575571

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

Dawei Teng1, Bo Wang, Alex J Augatis, Nancy I Totah.   

Abstract

An approach to the macrocyclic core of phomactin A is described. Central to this strategy is the use of a cis-fused oxadecalin intermediate, prepared using the dihydropyrone Diels-Alder reaction. The conformational bias inherent to this system is then used to facilitate macrocycle formation via an intramolecular B-alkyl Suzuki coupling.

Entities:  

Year:  2007        PMID： 18575571      PMCID： PMC2031845          DOI： 10.1016/j.tetlet.2007.04.122

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  Dihydropyrones as Dienophiles in the Diels-Alder Reaction: Application to the Synthesis of 1-Oxadecalones.

Authors:  Deqi Chen; Junquan Wang; Nancy I. Totah
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

2.  Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction.

Authors:  S R Chemler; U Iserloh; S J Danishefsky
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

3.  Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.

Authors:  Peter J Mohr; Randall L Halcomb
Journal:  J Am Chem Soc       Date:  2003-02-19       Impact factor: 15.419

4.  Unique structural topology and reactivities of the ABD tricycle in phomactin A.

Authors:  Kevin P Cole; Richard P Hsung
Journal:  Chem Commun (Camb)       Date:  2005-10-20       Impact factor: 6.222

5.  Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction.

Authors:  S R Chemler; S J Danishefsky
Journal:  Org Lett       Date:  2000-08-24       Impact factor: 6.005

6.  Use of thallium(I) ethoxide in Suzuki cross coupling reactions.

Authors:  S A Frank; H Chen; R K Kunz; M J Schnaderbeck; W R Roush
Journal:  Org Lett       Date:  2000-08-24       Impact factor: 6.005

7.  A novel class of platelet activating factor antagonists from Phoma sp.

Authors:  M Chu; I Truumees; I Gunnarsson; W R Bishop; W Kreutner; A C Horan; M G Patel; V P Gullo; M S Puar
Journal:  J Antibiot (Tokyo)       Date:  1993-04       Impact factor: 2.649

8.  Studies toward the tricyclic core of phomactin A. Synthesis of the reduced furanochroman subunit.

Authors:  P P Seth; N I Totah
Journal:  Org Lett       Date:  2000-08-10       Impact factor: 6.005

9.  Convergent enantioselective synthesis of the tricyclic core of phomactin A.

Authors:  Peter J Mohr; Randall L Halcomb
Journal:  Org Lett       Date:  2002-07-11       Impact factor: 6.005

10.  A total synthesis of phomactin A.

Authors:  William P D Goldring; Gerald Pattenden
Journal:  Chem Commun (Camb)       Date:  2002-08-21       Impact factor: 6.222
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  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.  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

4.  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

5.  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

6.  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

7.  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

8.  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.  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
  9 in total

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