Literature DB >> 26388654

Synthetic Studies to Lyngbouilloside: A Phosphate Tether-Mediated Synthesis of the Macrolactone Core.

Rambabu Chegondi1, Paul R Hanson1.   

Abstract

A concise synthetic pathway to the originally assigned structure of lyngbouilloside macrolactone (3) is reported. The core macrocycle 3 was synthesized via a phosphate tether-mediated, one-pot, sequential RCM/CM/chemoselective hydrogenation reaction, Roskamp homologation, and a high yielding Boeckman acylketene cyclization.

Entities:  

Keywords:  (−)-Lyngbouilloside; Metathesis; Phosphate Tether; Total Synthesis

Year:  2015        PMID： 26388654      PMCID： PMC4572573          DOI： 10.1016/j.tetlet.2015.01.109

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


  22 in total

1.  Total synthesis of nominal lyngbouilloside aglycon.

Authors:  Abdelatif ElMarrouni; Raphael Lebeuf; Julian Gebauer; Montserrat Heras; Stellios Arseniyadis; Janine Cossy
Journal:  Org Lett       Date:  2011-12-07       Impact factor: 6.005

2.  Multivalent activation in temporary phosphate tethers: a new tether for small molecule synthesis.

Authors:  Alan Whitehead; Matthew D McReynolds; Joel D Moore; Paul R Hanson
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

3.  Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses.

Authors:  Michael H Haukaas; George A O'Doherty
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

4.  A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.

Authors:  Phanindra K M Venukadasula; Rambabu Chegondi; Soma Maitra; Paul R Hanson
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

Authors:  Susanthi Jayasinghe; Phanindra K M Venukadasula; Paul R Hanson
Journal:  Org Lett       Date:  2013-12-02       Impact factor: 6.005

6.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

7.  Studies for the total synthesis of amphidinolide P.

Authors:  David R Williams; Brian J Myers; Liang Mi; Randall J Binder
Journal:  J Org Chem       Date:  2013-04-26       Impact factor: 4.354

8.  Lyngbouilloside, a novel glycosidic macrolide from the marine cyanobacterium Lyngbya bouillonii.

Authors:  Lik Tong Tan; Brian L Márquez; William H Gerwick
Journal:  J Nat Prod       Date:  2002-06       Impact factor: 4.050

9.  Lyngbyaloside B, a new glycoside macrolide from a Palauan marine cyanobacterium, Lyngbya sp.

Authors:  Hendrik Luesch; Wesley Y Yoshida; George G Harrigan; James P Doom; Richard E Moore; Valerie J Paul
Journal:  J Nat Prod       Date:  2002-12       Impact factor: 4.050

10.  A formal synthesis of the callipeltoside aglycone.

Authors:  James A Marshall; Patrick M Eidam
Journal:  Org Lett       Date:  2007-12-05       Impact factor: 6.005
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  7 in total

1.  Modular Synthesis of Novel Macrocycles Bearing α,β-Unsaturated Chemotypes through a Series of One-Pot, Sequential Protocols.

Authors:  Salim Javed; Mahipal Bodugam; Jessica Torres; Arghya Ganguly; Paul R Hanson
Journal:  Chemistry       Date:  2016-04-05       Impact factor: 5.236

2.  P-Tether-Mediated, Iterative SN2'-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative "Function Switch" with Phosphite-Borane Tethers.

Authors:  Jana L Markley; Paul R Hanson
Journal:  Org Lett       Date:  2017-05-04       Impact factor: 6.005

3.  Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large, P-Stereogenic Bicyclo[n.3.1]phosphates.

Authors:  Soma Maitra; Jana L Markley; Rambabu Chegondi; Paul R Hanson
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

4.  P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable P-Tether Systems for the Desymmetrization of C2-Symmetric 1,3-anti-Diols.

Authors:  Jana L Markley; Paul R Hanson
Journal:  Org Lett       Date:  2017-05-04       Impact factor: 6.005

5.  Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of P-Stereogenic, Z-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates.

Authors:  Jana L Markley; Soma Maitra; Paul R Hanson
Journal:  J Org Chem       Date:  2016-01-21       Impact factor: 4.354

6.  A Pot-Economical Approach to the Total Synthesis of Sch-725674.

Authors:  Mahipal Bodugam; Salim Javed; Arghya Ganguly; Jessica Torres; Paul R Hanson
Journal:  Org Lett       Date:  2016-01-13       Impact factor: 6.005

7.  Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Authors:  Soma Maitra; Mahipal Bodugam; Salim Javed; Paul R Hanson
Journal:  Org Lett       Date:  2016-06-14       Impact factor: 6.005
  7 in total

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