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Literature DB >> 19754145

Second generation synthesis of C27-C35 building block of E7389, a synthetic halichondrin analogue.

Yu-Rong Yang¹, Dae-Shik Kim, Yoshito Kishi.

Abstract

A practical method is reported to synthesize E7389 C27-C35 building block 13 from 1,2-O-isopropylidene-alpha-D-5-deoxyglucurono-6,3-lactone (3). This synthesis relies on two key processes: (1) C34/C35-diol is introduced via asymmetric dihydroxylation with dr = 3:1, with the undesired C34-diastereomer effectively removed by crystallization of 11, and (2) the C30 PhSO2CH2 group is introduced stereoselectively (>100:1) via hydrogenation of 12 in the presence of the Crabtree catalyst. The reported synthesis is practically free from chromatographic separation.

Entities: Chemical Disease Species

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Year: 2009 PMID： 19754145 PMCID： PMC2759418 DOI： 10.1021/ol9016589

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

12 in total

1. Highly 1,2-trans Stereoselective Allylations of 1,2-O-Isopropylidene-Protected Glycofuranosides This work was supported by the Canary Islands Consejería de Educación y Ciencia (PI1998/109), the Spanish Comisión Interministerial de Ciencia y Tecnología (PB98-0443-C02-02), and the FEDER (1SD97-0747-C04-01).

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-08-04 Impact factor: 15.336

2. 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

3. Halichondrin B: synthesis of the C1-C22 subunit.

Authors: William T Lambert; Gregory H Hanson; Farid Benayoud; Steven D Burke
Journal: J Org Chem Date: 2005-11-11 Impact factor: 4.354

4. Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

Authors: Kosuke Namba; Yoshito Kishi
Journal: J Am Chem Soc Date: 2005-11-09 Impact factor: 15.419

5. 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

6. Isolation and structure of the cell growth inhibitory constituents from the western Pacific marine sponge Axinella sp.

Authors: G R Pettit; C L Herald; M R Boyd; J E Leet; C Dufresne; D L Doubek; J M Schmidt; R L Cerny; J N Hooper; K C Rützler
Journal: J Med Chem Date: 1991-11 Impact factor: 7.446

7. A total synthesis of norhalichondrin B.

Authors: Katrina L Jackson; James A Henderson; Hajime Motoyoshi; Andrew J Phillips
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. 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

9. Antitumour polyether macrolides: four new halichondrins from the New Zealand deep-water marine sponge Lissodendoryx sp.

Authors: Sarah J H Hickford; John W Blunt; Murray H G Munro
Journal: Bioorg Med Chem Date: 2008-11-19 Impact factor: 3.641

Second generation synthesis of C27-C35 building block of E7389, a synthetic halichondrin analogue.

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

3. Halichondrin B: synthesis of the C1-C22 subunit.

4. Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

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

6. Isolation and structure of the cell growth inhibitory constituents from the western Pacific marine sponge Axinella sp.

7. A total synthesis of norhalichondrin B.

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

9. Antitumour polyether macrolides: four new halichondrins from the New Zealand deep-water marine sponge Lissodendoryx sp.

10. Attempts to improve the overall stereoselectivity of the Ireland-Claisen rearrangement.

Review 1. Modern natural products drug discovery and its relevance to biodiversity conservation.

2. A unified strategy for the total syntheses of eribulin and a macrolactam analogue of halichondrin B.

Review 3. Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.