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Literature DB >> 17286380

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

Abstract

An operationally simple and efficient workup method for tetrabutylammonium fluoride (TBAF)-mediated t-butyldimethylsilyl (TBS) deprotection has been developed. The procedure includes addition of a sulfonic acid resin and calcium carbonate, followed by filtration and evaporation. This method eliminates the tedious aqueous-phase extraction process to remove excess TBAF and materials derived from TBAF, thereby making the protocol highly amenable to multiple TBS deprotections. Its efficiency and usefulness were demonstrated by using the transformation of 1a to 3a in the halichondrin synthesis. [reaction: see text].

Entities: Chemical

Mesh：

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Year: 2007 PMID： 17286380 PMCID： PMC2519602 DOI： 10.1021/ol063113h

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

11 in total

Review 1. Natural products which interact with tubulin in the vinca domain: maytansine, rhizoxin, phomopsin A, dolastatins 10 and 15 and halichondrin B.

Authors: E Hamel
Journal: Pharmacol Ther Date: 1992 Impact factor: 12.310

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. Macrocyclic ketone analogues of halichondrin B.

Authors: Wanjun Zheng; Boris M Seletsky; Monica H Palme; Paul J Lydon; Lori A Singer; Charles E Chase; Charles A Lemelin; Yongchun Shen; Heather Davis; Lynda Tremblay; Murray J Towle; Kathleen A Salvato; Bruce F Wels; Kimberley K Aalfs; Yoshito Kishi; Bruce A Littlefield; Melvin J Yu
Journal: Bioorg Med Chem Lett Date: 2004-11-15 Impact factor: 2.823

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 mixed resin bed for the quenching and purification of tetrabutylammonium fluoride mediated desilylating reactions.

Authors: J J Parlow; M L Vazquez; D L Flynn
Journal: Bioorg Med Chem Lett Date: 1998-09-08 Impact factor: 2.823

8. The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth.

Authors: Mary Ann Jordan; Kathryn Kamath; Tapas Manna; Tatiana Okouneva; Herbert P Miller; Celia Davis; Bruce A Littlefield; Leslie Wilson
Journal: Mol Cancer Ther Date: 2005-07 Impact factor: 6.261

9. Interaction of halichondrin B and homohalichondrin B with bovine brain tubulin.

Authors: R F Ludueña; M C Roach; V Prasad; G R Pettit
Journal: Biochem Pharmacol Date: 1993-01-26 Impact factor: 5.858

10. Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data.

Authors: R L Bai; K D Paull; C L Herald; L Malspeis; G R Pettit; E Hamel
Journal: J Biol Chem Date: 1991-08-25 Impact factor: 5.157

15 in total

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

Review 1. Natural products which interact with tubulin in the vinca domain: maytansine, rhizoxin, phomopsin A, dolastatins 10 and 15 and halichondrin B.

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. Macrocyclic ketone analogues of halichondrin B.

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

7. A mixed resin bed for the quenching and purification of tetrabutylammonium fluoride mediated desilylating reactions.

8. The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth.

9. Interaction of halichondrin B and homohalichondrin B with bovine brain tubulin.

10. Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data.

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

2. Synthesis and structure assignment of the minor metabolite arising from the frog pathogen Mycobacterium liflandii.

3. Chemical and biological studies of nakiterpiosin and nakiterpiosinone.

4. Synthesis and structure revision of nakiterpiosin.

5. Effective Procedure for Selective Ammonolysis of Monosubstituted Oxiranes: Application to E7389 Synthesis.

6. A total synthesis of norhalichondrin B.

7. Kinetically controlled E-selective catalytic olefin metathesis.

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

9. Solid-phase synthesis of alpha-glucosamine sulfoforms with fragmentation analysis by tandem mass spectrometry.

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