Literature DB >> 20121257

Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.

Sipak Joyasawal1, Stephen D Lotesta, N G Akhmedov, Lawrence J Williams.   

Abstract

The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.

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Year:  2010        PMID： 20121257      PMCID： PMC3050037          DOI： 10.1021/ol902984e

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


  26 in total

Review 1.  The remarkable metal-catalysed olefin metathesis reaction.

Authors:  Amir H Hoveyda; Adil R Zhugralin
Journal:  Nature       Date:  2007-11-08       Impact factor: 49.962

2.  A concise total synthesis of melithiazole C.

Authors:  Julian Gebauer; Stellios Arseniyadis; Janine Cossy
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005

3.  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 4.  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

5.  Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation.

Authors:  W J Kerr; M McLaughlin; A J Morrison; P L Pauson
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

6.  Asymmetric synthesis of bicyclic beta-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization: improved efficiency and expanded scope.

Authors:  Seong Ho Oh; Guillermo S Cortez; Daniel Romo
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

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.  A formal synthesis of psymberin.

Authors:  Ning Shangguan; Sezgin Kiren; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-24       Impact factor: 6.005

9.  A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4.

Authors:  Stephen D Lotesta; Yongquan Hou; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-08       Impact factor: 6.005

10.  Spirodiepoxides: synthesis of epoxomicinoids.

Authors:  Yue Zhang; Joseph R Cusick; Partha Ghosh; Ning Shangguan; Sreenivas Katukojvala; Jennifer Inghrim; Thomas J Emge; Lawrence J Williams
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354
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  9 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Synthesis of 1,3-diaminated stereotriads via rearrangement of 1,4-diazaspiro[2.2]pentanes.

Authors:  Cale D Weatherly; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2012-03-20       Impact factor: 6.005

3.  Spirodiepoxide-based cascades: direct access to diverse motifs.

Authors:  Rojita Sharma; Madhuri Manpadi; Yue Zhang; Hiyun Kim; Novruz G Ahkmedov; Lawrence J Williams
Journal:  Org Lett       Date:  2011-06-07       Impact factor: 6.005

4.  Modular functionalization of allenes to aminated stereotriads.

Authors:  Christopher S Adams; Luke A Boralsky; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-06-20       Impact factor: 15.419

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

Authors:  Daniel P Canterbury; Glenn C Micalizio
Journal:  Org Lett       Date:  2011-04-08       Impact factor: 6.005

6.  Direct entry to erythronolides via a cyclic bis[allene].

Authors:  Kai Liu; Hiyun Kim; Partha Ghosh; Novruz G Akhmedov; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2011-09-06       Impact factor: 15.419

7.  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

8.  Toward an integrated route to the vernonia allenes and related sesquiterpenoids.

Authors:  Da Xu; Michael A Drahl; Lawrence J Williams
Journal:  Beilstein J Org Chem       Date:  2011-07-05       Impact factor: 2.883

9.  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
  9 in total

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