Literature DB >> 21476517

A convergent route to the CDEF-tetracycle of pectenotoxin-2.

Daniel P Canterbury1, Glenn C Micalizio.   

Abstract

A convergent synthesis of the CDEF-tetracyclic region of pectenotoxin-2 (PTX-2) is described. The synthetic pathway derives from a head-to-tail union of 2 equiv of linalool to establish a stereodefined DEF-tricyclic aldehyde. Subsequent coupling with a "northern" fragment enolate, followed by a tandem Sharpless epoxidation/cyclization, delivers the C10-C26 polycyclic region of the natural product.

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Year:  2011        PMID： 21476517      PMCID： PMC3156112          DOI： 10.1021/ol200627d

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


  39 in total

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Authors:  Guofu Zhong
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-15       Impact factor: 15.336

2.  Synthetic studies toward pectenotoxin 2. Part I. Stereocontrolled access to the C10-C22 fragment.

Authors:  Jatta E Aho; Elina Salomäki; Kari Rissanen; Petri M Pihko
Journal:  Org Lett       Date:  2008-09-03       Impact factor: 6.005

Review 3.  Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.

Authors:  O Andrea Wong; Yian Shi
Journal:  Chem Rev       Date:  2008-07-01       Impact factor: 60.622

4.  Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

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Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

5.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

6.  Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Authors:  Kanicha Sa-ei; John Montgomery
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

7.  Pectenotoxin-2 synthetic studies. 3. Assessment of the capacity for stereocontrolled cyclization to form the entire C1-C26 subunit based upon the double bond geometry across C15-C16.

Authors:  Patrick D O'Connor; Christopher K Knight; Dirk Friedrich; Xiaowen Peng; Leo A Paquette
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

8.  Studies on the syntheses of benzoquinone ansamycin antibiotics. Syntheses of the C5-C15 subunits of macbecin I, geldanamycin, and herbimycin A.

Authors:  Justin K Belardi; Glenn C Micalizio
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

9.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

10.  Lactone ring of pectenotoxins: a key factor for their activity on cytoskeletal dynamics.

Authors:  Isabel R Ares; M Carmen Louzao; Begoña Espiña; Mercedes R Vieytes; Christopher O Miles; Takeshi Yasumoto; Luis M Botana
Journal:  Cell Physiol Biochem       Date:  2007
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  2 in total

1.  Synthesis of the C1-C26 hexacyclic subunit of pectenotoxin 2.

Authors:  Ozora Kubo; Daniel P Canterbury; Glenn C Micalizio
Journal:  Org Lett       Date:  2012-10-26       Impact factor: 6.005

2.  Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone.

Authors:  Natasha F O'Rourke; Mu A; Henry N Higgs; Alan Eastman; Glenn C Micalizio
Journal:  Org Lett       Date:  2017-09-13       Impact factor: 6.005
  2 in total

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