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Literature DB >> 22356535

Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

Abstract

A catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal synthesis of aspergillide B in a highly efficient manner.

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Year: 2012 PMID： 22356535 PMCID： PMC3407809 DOI： 10.1021/ol300200m

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

24 in total

1. A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes.

Authors: N K Anand; E M Carreira
Journal: J Am Chem Soc Date: 2001-10-03 Impact factor: 15.419

2. Routine use of natural abundance deuterium NMR in a polypeptidic chiral oriented solvent for the determination of the enantiomeric composition of chiral building blocks.

Authors: Arnaud Parenty; Jean-Marc Campagne; Christie Aroulanda; Philippe Lesot
Journal: Org Lett Date: 2002-05-16 Impact factor: 6.005

3. Enantioselective synthesis of aspergillide B.

Authors: Tomohiro Nagasawa; Shigefumi Kuwahara
Journal: Biosci Biotechnol Biochem Date: 2009-08-07 Impact factor: 2.043

4. A unified total synthesis of aspergillides A and B.

Authors: Haruhiko Fuwa; Hiroshi Yamaguchi; Makoto Sasaki
Journal: Org Lett Date: 2010-04-16 Impact factor: 6.005

5. Total synthesis of aspergillide A and B based on the transannular oxy-Michael reaction.

Authors: Makoto Kanematsu; Masahiro Yoshida; Kozo Shishido
Journal: Angew Chem Int Ed Engl Date: 2011-02-15 Impact factor: 15.336

Review 6. The discovery of novel reactivity in the development of C-C bond-forming reactions: in situ generation of zinc acetylides with Zn(II)/R(3)N.

Authors: D E Frantz; R Fassler; C S Tomooka; E M Carreira
Journal: Acc Chem Res Date: 2000-06 Impact factor: 22.384

7. Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.

Authors: Barry M Trost; Julien Hitce
Journal: J Am Chem Soc Date: 2009-04-08 Impact factor: 15.419

8. Enantioselective formal total synthesis of (+)-aspergillide C.

Authors: Joseph D Panarese; Stephen P Waters
Journal: Org Lett Date: 2009-11-05 Impact factor: 6.005

9. Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis.

Authors: Fei Yang; Peihua Xi; Li Yang; Jingbo Lan; Rugang Xie; Jingsong You
Journal: J Org Chem Date: 2007-06-08 Impact factor: 4.354

10. Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.

Authors: Ge Gao; Ru-Gang Xie; Lin Pu
Journal: Proc Natl Acad Sci U S A Date: 2004-03-16 Impact factor: 11.205

7 in total

7. Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.

Authors: Michael Mulzer; Brandon J Tiegs; Yanping Wang; Geoffrey W Coates; George A O'Doherty
Journal: J Am Chem Soc Date: 2014-07-18 Impact factor: 15.419

7 in total

Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

1. A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes.

2. Routine use of natural abundance deuterium NMR in a polypeptidic chiral oriented solvent for the determination of the enantiomeric composition of chiral building blocks.

3. Enantioselective synthesis of aspergillide B.

4. A unified total synthesis of aspergillides A and B.

5. Total synthesis of aspergillide A and B based on the transannular oxy-Michael reaction.

Review 6. The discovery of novel reactivity in the development of C-C bond-forming reactions: in situ generation of zinc acetylides with Zn(II)/R(3)N.

7. Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.

8. Enantioselective formal total synthesis of (+)-aspergillide C.

9. Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis.

10. Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.

1. Asymmetric catalytic alkynylation of acetaldehyde: application to the synthesis of (+)-tetrahydropyrenophorol.

2. Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

3. Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

4. ProPhenol-catalyzed asymmetric additions by spontaneously assembled dinuclear main group metal complexes.

5. A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.

6. Synthesis of a simplified triazole analogue of pateamine A.

7. Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.