Literature DB >> 23249423

Enantioselective synthesis of the C1-C11 fragment of tedanolide C.

Julie G Geist1, Roland Barth, William R Roush.   

Abstract

A convergent synthesis of the protected C(1)-C(11) fragment 6 of the targeted enantiomer of tedanolide C is described. The key step of the synthesis is the Felkin-Ahn addition of vinyl iodide 7 to aldehyde 8 that proceeds in 80% yield with 4:1 diastereoselectivity.

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Year:  2012        PMID： 23249423      PMCID： PMC3539184          DOI： 10.1021/ol303089w

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


  17 in total

1.  Diastereoselective additions of chiral vinylzinc reagents to alpha-chiral aldehydes.

Authors:  James A Marshall; Patrick Eidam
Journal:  Org Lett       Date:  2004-02-05       Impact factor: 6.005

2.  The synthesis of deoxyfusapyrone. 2. Preparation of the bis-trisubstituted olefin fragment and its attachment to the pyrone moiety.

Authors:  Michael G Organ; Junquan Wang
Journal:  J Org Chem       Date:  2003-07-11       Impact factor: 4.354

3.  A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach.

Authors:  Kay M Brummond; Sang-phyo Hong
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

4.  Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Satoru Yoshida; Yoichi Nakao; Hiroshi Hirota; Nobuhiro Fusetani
Journal:  Bioorg Med Chem       Date:  2005-01-17       Impact factor: 3.641

5.  Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

Authors:  M T Crimmins; B W King; E A Tabet; K Chaudhary
Journal:  J Org Chem       Date:  2001-02-09       Impact factor: 4.354

6.  13-Deoxytedanolide, a marine sponge-derived antitumor macrolide, binds to the 60S large ribosomal subunit.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Minoru Yoshida; Hiroshi Hirota; Shigeyuki Yokoyama; Nobuhiro Fusetani
Journal:  Bioorg Med Chem       Date:  2005-01-17       Impact factor: 3.641

7.  Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C.

Authors:  Thomas E Smith; Sarah J Fink; Zebulon G Levine; Kerani A McClelland; Adrian A Zackheim; Mary E Daub
Journal:  Org Lett       Date:  2012-02-29       Impact factor: 6.005

8.  Candidaspongiolides, distinctive analogues of tedanolide from sponges of the genus Candidaspongia.

Authors:  Tamara L Meragelman; Richard H Willis; Girma M Woldemichael; Andrew Heaton; Peter T Murphy; Kenneth M Snader; David J Newman; Rob van Soest; Michael R Boyd; John H Cardellina; Tawnya C McKee
Journal:  J Nat Prod       Date:  2007-06-12       Impact factor: 4.050

9.  Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

Authors:  Thomas R Hoye; Christopher S Jeffrey; Feng Shao
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

10.  Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp.

Authors:  Camille Chevallier; Tim S Bugni; Xidong Feng; Mary Kay Harper; Anita M Orendt; Chris M Ireland
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354
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  1 in total

Review 1.  Recent developments in the asymmetric Reformatsky-type reaction.

Authors:  Hélène Pellissier
Journal:  Beilstein J Org Chem       Date:  2018-02-02       Impact factor: 2.883
  1 in total

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