Literature DB >> 19260663

Total synthesis of phomactin A.

Yu Tang1, Kevin P Cole, Grant S Buchanan, Gang Li, Richard P Hsung.   

Abstract

A total synthesis of (+/-)-phomactin A is described to highlight the final completion of a complex natural product target that had commenced with an intramolecular oxa-[3 + 3] annulation strategy in the construction of the ABD-tricycle. These efforts reveal structural intricacies of this ABD-tricycle with an illustrative example being the conformational analysis that was ultimately critical for the C5a-homolgation.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19260663      PMCID： PMC2701356          DOI： 10.1021/ol900237e

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


  42 in total

1.  An unusual cationic [2 + 2] cycloaddition in a divergent total synthesis of hongoquercin A and rhododaurichromanic acid A.

Authors:  Aleksey V Kurdyumov; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

2.  A Sakurai-Prins-Ritter sequence for the three-component diastereoselective synthesis of 4-amino tetrahydropyrans.

Authors:  Oleg L Epstein; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

3.  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

4.  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

5.  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

6.  Broadly effective enantioselective Diels-Alder reactions of 1-amino-substituted-1,3-butadienes.

Authors:  Yong Huang; Tetsuo Iwama; Viresh H Rawal
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

7.  A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) coupling approach to the phomactins.

Authors:  B Mi; R E Maleczka
Journal:  Org Lett       Date:  2001-05-17       Impact factor: 6.005

8.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

9.  A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues.

Authors:  Hongjuan Hu; Tyler J Harrison; Peter D Wilson
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

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
View more
  10 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.  Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

Authors:  Gang Li; Dasheng Leow; Li Wan; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-13       Impact factor: 15.336

3.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       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.  Total Syntheses of Proposed (±)-Trichodermatides B and C.

Authors:  Qian Li; Yan-Shuang Xu; Gregory A Ellis; Timothy S Bugni; Yu Tang; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2013-10-09       Impact factor: 2.415

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

Review 10.  Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products.

Authors:  Alexander O Terent'ev; Dmitry A Borisov; Vera A Vil'; Valery M Dembitsky
Journal:  Beilstein J Org Chem       Date:  2014-01-08       Impact factor: 2.883
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.