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Literature DB >> 20548799

A synthesis of the C1-C15 domain of the halichondrins.

Katrina L Jackson¹, James A Henderson, Jonathan C Morris, Hajime Motoyoshi, Andrew J Phillips.

Abstract

A concise route to the C1-C15 domain of the halichondrins is described. The key reaction is the conversion of a furfuryl alcohol to a pyranone. The stereocenter of this pyranone serves as the starting point for the other 8 stereocenters.

Entities: Chemical

Year: 2008 PMID： 20548799 PMCID： PMC2884163 DOI： 10.1016/j.tetlet.2008.03.018

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

6 in total

1. A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

Authors: Kosuke Namba; Hyuk-Sang Jun; Yoshito Kishi
Journal: J Am Chem Soc Date: 2004-06-30 Impact factor: 15.419

2. Total syntheses of ipomoeassin B and E.

Authors: Alois Fürstner; Takashi Nagano
Journal: J Am Chem Soc Date: 2007-01-25 Impact factor: 15.419

3. Highly functionalized pyranopyrans from furans: a synthesis of the C27-C38 and C44-C53 subunits of norhalichondrin B.

Authors: James A Henderson; Katrina L Jackson; Andrew J Phillips
Journal: Org Lett Date: 2007-11-14 Impact factor: 6.005

4. Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions.

Authors: J M Harris; M D Keränen; H Nguyen; V G Young; G A O'Doherty
Journal: Carbohydr Res Date: 2000-08-18 Impact factor: 2.104

5. Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry.

Authors: Valerie A Keller; Ikyon Kim; Steven D Burke
Journal: Org Lett Date: 2005-02-17 Impact factor: 6.005

6. Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

Authors: Yosuke Kaburagi; Yoshito Kishi
Journal: Org Lett Date: 2007-02-15 Impact factor: 6.005

6 in total

4 in total

A synthesis of the C1-C15 domain of the halichondrins.

1. A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

2. Total syntheses of ipomoeassin B and E.

3. Highly functionalized pyranopyrans from furans: a synthesis of the C27-C38 and C44-C53 subunits of norhalichondrin B.

4. Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions.

5. Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry.

6. Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

1. Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

2. A total synthesis of norhalichondrin B.

3. One-pot catalytic asymmetric synthesis of pyranones.

4. Electrocatalytic synthesis of heterocycles from biomass-derived furfuryl alcohols.