Literature DB >> 20681603

Total synthesis of lehualide B by allylic alcohol-alkyne reductive cross-coupling.

Valer Jeso1, Glenn C Micalizio.   

Abstract

The total synthesis of anticancer marine natural product lehualide B is described. Overall, the synthesis proceeds in just eight steps from a simple gamma-pyrone, does not require the use of protecting groups, and delivers each nonconjugated trisubstituted alkene with high levels of stereoselection. The challenging C12-C16 bis-trisubstituted 1,4-diene was installed with a complex reductive cross-coupling reaction between a preformed Ti-alkyne complex and a pyrone-containing allylic alcohol.

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Year:  2010        PMID： 20681603      PMCID： PMC2923668          DOI： 10.1021/ja104782u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  5 in total

1.  Total synthesis of piericidin A1 and B1 and key analogues.

Authors:  Martin J Schnermann; F Anthony Romero; Inkyu Hwang; Eiko Nakamaru-Ogiso; Takao Yagi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

2.  Synthesis of substituted 1,4-dienes by direct alkylation of allylic alcohols.

Authors:  Filip Kolundzic; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2007-11-16       Impact factor: 15.419

3.  Total synthesis and structure elucidation of (+)-phorbasin C.

Authors:  Todd K Macklin; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

4.  Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors:  Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal:  European J Org Chem       Date:  2010-01

5.  Lehualides A-D, metabolites from a Hawaiian sponge of the genus Plakortis.

Authors:  Noriko Sata; Hazel Abinsay; Wesley Y Yoshida; F David Horgen; Namthip Sitachitta; Michelle Kelly; Paul J Scheuer
Journal:  J Nat Prod       Date:  2005-09       Impact factor: 4.803
  5 in total
  12 in total

1.  Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade.

Authors:  Haruki Mizoguchi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

2.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

3.  Synthesis and SAR of Lehualide B: a marine-derived natural product with potent anti-multiple myeloma activity.

Authors:  Valer Jeso; Chunying Yang; Michael D Cameron; John L Cleveland; Glenn C Micalizio
Journal:  ACS Chem Biol       Date:  2013-04-02       Impact factor: 5.100

4.  A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.

Authors:  Zachary A Shalit; Glenn C Micalizio
Journal:  ARKIVOC       Date:  2018-03-28       Impact factor: 1.140

5.  Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids.

Authors:  Matthew S McCammant; Takashi Shigeta; Matthew S Sigman
Journal:  Org Lett       Date:  2016-03-28       Impact factor: 6.005

6.  Convergent synthesis of deoxypropionates.

Authors:  Peter S Diez; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-05       Impact factor: 15.336

7.  Metallacycle-Mediated Cross-Coupling with Substituted and Electronically Unactivated Alkenes.

Authors:  Holly A Reichard; Glenn C Micalizio
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

8.  Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.

Authors:  Zhanjie Li; Brendan T Parr; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

9.  Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors:  Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-03-12       Impact factor: 15.419

10.  Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols.

Authors:  Dexi Yang; Glenn C Micalizio
Journal:  Chem Commun (Camb)       Date:  2013-10-09       Impact factor: 6.222
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