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Literature DB >> 22950417

An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

Tyler J Harrison¹, Philippe M A Rabbat, James L Leighton.

Abstract

An efficient synthesis of the C(1)-C(9) fragment of fludelone has been developed. The key step is a tandem silylformylation-crotylsilylation/Tamao oxidation sequence that establishes the C(5) ketone, the C(6), C(7), and C(8) stereocenters, and the C(9) alkene in a single operation from a readily accessed starting material. The stereochemical outcome at C(6) depends critically on the development of an "aprotic" Tamao oxidation, which leads to a reversal in the intrinsic diastereoselectivity observed using "standard" Tamao oxidation conditions.

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Year: 2012 PMID： 22950417 PMCID： PMC3466590 DOI： 10.1021/ol302221s

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

15 in total

1. Tandem Intramolecular Alkyne Silylformylation-Allylsilylation: A Case of Remote 1,5-Asymmetric Induction Financial support was provided by the National Institutes of Health (National Institute of General Medical Sciences, GM58133). We are grateful to Bristol-Myers Squibb for generous financial support in the form of an Unrestricted Grant in Synthetic Organic Chemistry to J.L.L. We thank Merck Research Laboratories and DuPont Pharmaceuticals for generous financial support.

Authors: Steven J. O'Malley; James L. Leighton
Journal: Angew Chem Int Ed Engl Date: 2001-08-03 Impact factor: 15.336

2. Tandem aldol-allylation and aldol-aldol reactions with ketone-derived enolsilanes: highly diastereoselective single-step synthesis of complex tertiary carbinols.

Authors: Xiaolun Wang; Qinglin Meng; Nicholas R Perl; Yue Xu; James L Leighton
Journal: J Am Chem Soc Date: 2005-09-21 Impact factor: 15.419

Review 3. On the remarkable antitumor properties of fludelone: how we got there.

Authors: Alexey Rivkin; Ting-Chao Chou; Samuel J Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2005-05-06 Impact factor: 15.336

4. Discovery of (E)-9,10-dehydroepothilones through chemical synthesis: on the emergence of 26-trifluoro-(E)-9,10-dehydro-12,13-desoxyepothilone B as a promising anticancer drug candidate.

Authors: Alexey Rivkin; Fumihiko Yoshimura; Ana E Gabarda; Young Shin Cho; Ting-Chao Chou; Huajin Dong; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2004-09-08 Impact factor: 15.419

5. Synthesis and biological activity of photoactivatable N-ras peptides and proteins.

Authors: Martin Völkert; Koji Uwai; Andreas Tebbe; Boriana Popkirova; Melanie Wagner; Jürgen Kuhlmann; Herbert Waldmann
Journal: J Am Chem Soc Date: 2003-10-22 Impact factor: 15.419

6. Strained silacycles in organic synthesis: the tandem aldol-allylation reaction.

Authors: Xiaolun Wang; Qinglin Meng; Andrew J Nation; James L Leighton
Journal: J Am Chem Soc Date: 2002-09-11 Impact factor: 15.419

7. Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions.

Authors: Cheng Zhu; Xiaoqiang Shen; Scott G Nelson
Journal: J Am Chem Soc Date: 2004-05-05 Impact factor: 15.419

8. Catalytic asymmetric silane alcoholysis: practical access to chiral silanes.

Authors: Darby R Schmidt; Steven J O'Malley; James L Leighton
Journal: J Am Chem Soc Date: 2003-02-05 Impact factor: 15.419

9. An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

Authors: Shuangyi Wan; Hakan Gunaydin; K N Houk; Paul E Floreancig
Journal: J Am Chem Soc Date: 2007-06-05 Impact factor: 15.419

10. Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

Authors: Jared T Spletstoser; Michael J Zacuto; James L Leighton
Journal: Org Lett Date: 2008-12-18 Impact factor: 6.005

6 in total

An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

2. Tandem aldol-allylation and aldol-aldol reactions with ketone-derived enolsilanes: highly diastereoselective single-step synthesis of complex tertiary carbinols.

Review 3. On the remarkable antitumor properties of fludelone: how we got there.

4. Discovery of (E)-9,10-dehydroepothilones through chemical synthesis: on the emergence of 26-trifluoro-(E)-9,10-dehydro-12,13-desoxyepothilone B as a promising anticancer drug candidate.

5. Synthesis and biological activity of photoactivatable N-ras peptides and proteins.

6. Strained silacycles in organic synthesis: the tandem aldol-allylation reaction.

7. Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions.

8. Catalytic asymmetric silane alcoholysis: practical access to chiral silanes.

9. An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

10. Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

1. Synthesis and Evaluation of a Linkable Functional Group-Equipped Analogue of the Epothilones.

2. A Highly Stereoselective, Efficient, and Scalable Synthesis of the C(1)-C(9) Fragment of the Epothilones.

3. A highly step-economical synthesis of dictyostatin.

4. Tailoring chemoenzymatic oxidation via in situ peracids.

5. Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis.

6. Stereoselective one-pot synthesis of polypropionates.