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Literature DB >> 11975524

Total synthesis of (-)-callystatin A.

Abstract

A total synthesis of the cytotoxic polyketide marine natural product callystatin A is described. The route features chiral allenylmetal additions to construct the polypropionate C15-22 segment and an sp(2)-sp(3) Suzuki coupling to join the C1-C11 and C12-C22 subunits.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 11975524 DOI： 10.1021/jo016025d

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

7 in total

Review 1. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

2. 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

3. Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors: Ming Chen; William R Roush
Journal: J Am Chem Soc Date: 2012-06-25 Impact factor: 15.419

4. Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

Authors: Zhihong Huang; Ei-ichi Negishi
Journal: J Am Chem Soc Date: 2007-11-07 Impact factor: 15.419

Total synthesis of (-)-callystatin A.

Review 1. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

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

3. Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

4. Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

5. Total synthesis of piericidin A1. Application of a modified Negishi carboalumination-nickel-catalyzed cross-coupling.

6. A versatile route to the tulearin class of macrolactones: synthesis of a stereoisomer of tulearin A.

Review 7. Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.