Literature DB >> 18076184

Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step.

Eun Jin Cho1, Daesung Lee.   

Abstract

Enyne metathesis is unique for its capacity to carry out multiple bond formation in tandem fashion. Its combined use with metallotropic [1,3]-shift allowed for the development of a novel strategy for the total synthesis of a conjugated 1,3-diyne-containing natural product (3R,9R,10R)-panaxytriol.

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Year:  2007        PMID： 18076184      PMCID： PMC2525611          DOI： 10.1021/ol702651s

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


  31 in total

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Authors:  B M Trost; F D Toste; A B Pinkerton
Journal:  Chem Rev       Date:  2001-07       Impact factor: 60.622

2.  First approach to the frondosin C ring system via a tandem cyclization/Claisen rearrangement sequence.

Authors:  Isamir Martínez; Philip E Alford; Timo V Ovaska
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

3.  Progress toward the total synthesis of frondosin C.

Authors:  Xin Li; Robert E Kyne; Timo V Ovaska
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

4.  Total synthesis as a resource in drug discovery: the first in vivo evaluation of panaxytriol and its derivatives.

Authors:  Heedong Yun; Ting-Chao Chou; Huajin Dong; Yuan Tian; Yue-ming Li; Samuel J Danishefsky
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

5.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

6.  [Chemical studies of crude drugs (1). Constituents of Ginseng radix rubra].

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Review 7.  Synthesis of naturally occurring polyynes.

Authors:  Annabelle L K Shi Shun; Rik R Tykwinski
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-06       Impact factor: 15.336

8.  Substituent effects on the Z/E-selectivity in cross-metathesis of conjugated enynes.

Authors:  Byungman Kang; Ji Min Lee; Jaesik Kwak; Yoon Sup Lee; Sukbok Chang
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

9.  Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction.

Authors:  Sandra F Mayer; Andreas Steinreiber; Romano V A Orru; Kurt Faber
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

10.  A possible mechanism for the cytotoxicity of a polyacetylenic alcohol, panaxytriol: inhibition of mitochondrial respiration.

Authors:  H Matsunaga; T Saita; F Nagumo; M Mori; M Katano
Journal:  Cancer Chemother Pharmacol       Date:  1995       Impact factor: 3.333
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  6 in total

1.  Enantioselective ProPhenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products.

Authors:  Barry M Trost; Vincent S Chan; Daisuke Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

2.  (3R, 9R, 10R)-Panaxytriol: A molecular-based nutraceutical with possible application to cancer prevention and treatment.

Authors:  Fay Ng; Heedong Yun; Xiaoguang Lei; Samuel J Danishefsky; Jed Fahey; Katherine Stephenson; Charles Flexner; Lawrence Lee
Journal:  Tetrahedron Lett       Date:  2008-12-08       Impact factor: 2.415

3.  Structure and reactivity of alkynyl ruthenium alkylidenes.

Authors:  Sang Young Yun; Mansuk Kim; Daesung Lee; Donald J Wink
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

4.  Tandem enyne metathesis-metallotropic [1,3]-shift for a concise total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A.

Authors:  Jingwei Li; Sangho Park; Reagan L Miller; Daesung Lee
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

5.  Structure and reactivity of alkyne-chelated ruthenium alkylidene complexes.

Authors:  Kung-Pern Wang; Sang Young Yun; Daesung Lee; Donald J Wink
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419

6.  A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Authors:  Qiuzhe Xie; Richard W Denton; Kathlyn A Parker
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005
  6 in total

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