Literature DB >> 17580880

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

Jie Huang1, Huan Wang, Chunrui Wu, William D Wulff.   

Abstract

The intramolecular cyclohexadienone annulation of chromium carbene complexes is examined as a method to provide general access to the Phomactin family of natural products. The importance of the stereochemistry of the carbene complex and the number of carbons in the tether connecting the carbene complex and the alkyne are probed. Additionally, the degree of the 1,4-asymmetric induction is examined.

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Year:  2007        PMID： 17580880      PMCID： PMC2528892          DOI： 10.1021/ol070904q

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


  24 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.  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

Review 4.  The phomactins. A novel group of terpenoid platelet activating factor antagonists related biogenetically to the taxanes.

Authors:  William P D Goldring; Gerald Pattenden
Journal:  Acc Chem Res       Date:  2006-05       Impact factor: 22.384

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.  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

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.  Proposed mechanism for diterpene synthases in the formation of phomactatriene and taxadiene.

Authors:  Tetsuo Tokiwano; Taeko Endo; Tae Tsukagoshi; Hitoshi Goto; Eri Fukushi; Hideaki Oikawa
Journal:  Org Biomol Chem       Date:  2005-06-21       Impact factor: 3.876

9.  The first examples of a meta-benzannulation from the reaction of Fischer carbene complexes with alkynes.

Authors:  Huan Wang; Jie Huang; William D Wulff; Arnold L Rheingold
Journal:  J Am Chem Soc       Date:  2003-07-30       Impact factor: 15.419

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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  8 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 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.  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

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.  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

Review 8.  Synthesis of spirocyclic scaffolds using hypervalent iodine reagents.

Authors:  Fateh V Singh; Priyanka B Kole; Saeesh R Mangaonkar; Samata E Shetgaonkar
Journal:  Beilstein J Org Chem       Date:  2018-07-17       Impact factor: 2.883
  8 in total

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