Literature DB >> 22021939

Sporolide B: Synthetic Studies.

Jeffery A Gladding1, James P Bacci, Scott A Shaw, Amos B Smith.   

Abstract

Studies directed towards the synthesis of the architecturally complex marine natural product sporolide B are described. Synthetic analysis suggested advanced hydroquinone and benzodiquinane fragments, which upon elaboration were successfully united via an ester linkage. Macrocyclization studies were then carried out, and although a novel macrocyclization product was obtained, subsequent studies revealed that the tertiary hydroxyls at C(6) and C(10) were sterically encumbered to participate in a successful macrocyclization to furnish sporolide B.

Entities:  

Year:  2011        PMID： 22021939      PMCID： PMC3197724          DOI： 10.1016/j.tet.2011.04.094

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  22 in total

1.  Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors:  Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-20       Impact factor: 15.336

2.  Structure of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells.

Authors:  S Omura; K Matsuzaki; T Fujimoto; K Kosuge; T Furuya; S Fujita; A Nakagawa
Journal:  J Antibiot (Tokyo)       Date:  1991-01       Impact factor: 2.649

3.  Total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin.

Authors:  Xiaoguang Lei; Richard P Johnson; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-25       Impact factor: 15.336

4.  Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors:  Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-06-05       Impact factor: 15.419

5.  Synthesis and antitumor and antibacterial activity of benzoquinones related to the mitomycins.

Authors:  T R Witty; W A Remers
Journal:  J Med Chem       Date:  1973-11       Impact factor: 7.446

6.  Total synthesis of salinosporamide A.

Authors:  Atsushi Endo; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

7.  Synthesis of the sporolide ring framework through a cascade sequence involving an intramolecular [4+2] cycloaddition reaction of an o-quinone.

Authors:  K C Nicolaou; Jianhua Wang; Yefeng Tang
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052).

Authors:  Taotao Ling; Venkat R Macherla; Rama Rao Manam; Katherine A McArthur; Barbara C M Potts
Journal:  Org Lett       Date:  2007-05-12       Impact factor: 6.005

9.  A simple stereocontrolled synthesis of salinosporamide A.

Authors:  Leleti Rajender Reddy; P Saravanan; E J Corey
Journal:  J Am Chem Soc       Date:  2004-05-26       Impact factor: 15.419

10.  Unraveling the biosynthesis of the sporolide cyclohexenone building block.

Authors:  Ryan P McGlinchey; Markus Nett; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2008-01-31       Impact factor: 15.419
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  1 in total

1.  Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin.

Authors:  Daniel T Hog; Florian M E Huber; Gonzalo Jiménez-Osés; Peter Mayer; Kendall N Houk; Dirk Trauner
Journal:  Chemistry       Date:  2015-08-20       Impact factor: 5.236
  1 in total

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