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Literature DB >> 17944478

Synthesis of the C1-C52 fragment of amphidinol 3, featuring a beta-alkoxy alkyllithium addition reaction.

John R Huckins¹, Javier de Vicente, Scott D Rychnovsky.

Abstract

An advanced intermediate for the synthesis of amphidinol 3 has been prepared. A cross-metathesis reaction was used to couple the C1-C12 and C13-C26 segments. An unusual beta-alkoxy alkyllithium reagent was generated from this segment and added to a Weinreb amide to assemble the C1-C52 section of amphidinol 3. These compounds represent some of the most advanced intermediates reported to date for the synthesis of amphidinol 3.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17944478 PMCID： PMC2496920 DOI： 10.1021/ol7020934

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

10 in total

1. Chemoselective cross-metathesis reaction. Application to the synthesis of the C1-C14 fragment of amphidinol 3.

Authors: S BouzBouz; J Cossy
Journal: Org Lett Date: 2001-05-17 Impact factor: 6.005

2. A C-glycosidation approach to the central core of amphidinol 3: synthesis of the c39-c52 fragment.

Authors: Javier de Vicente; Bodo Betzemeier; Scott D Rychnovsky
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

3. The polyol domain of amphidinol 3. A stereoselective synthesis of the entire C(1)-C(30) sector.

Authors: Leo A Paquette; Shuh-Kuen Chang
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

4. Development of an access route to the c31-c52 central core of amphidinol 3.

Authors: Matthew W Bedore; Shuh-Kuen Chang; Leo A Paquette
Journal: Org Lett Date: 2007-02-01 Impact factor: 6.005

5. Synthesis of the C31-C67 fragment of amphidinol 3.

Authors: Javier de Vicente; John R Huckins; Scott D Rychnovsky
Journal: Angew Chem Int Ed Engl Date: 2006-11-06 Impact factor: 15.336

Review 6. Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors: L Pu; H B Yu
Journal: Chem Rev Date: 2001-03 Impact factor: 60.622

7. Synthesis of the C(43)-C(67) fragment of amphidinol 3.

Authors: Jacqueline D Hicks; Eric M Flamme; William R Roush
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

8. Synthesis of the C(1)-C(25) fragment of amphidinol 3: application of the double-allylboration reaction for synthesis of 1,5-diols.

Authors: Eric M Flamme; William R Roush
Journal: Org Lett Date: 2005-03-31 Impact factor: 6.005

9. Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors: Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal: J Org Chem Date: 1999-02-05 Impact factor: 4.354

10. A general model for selectivity in olefin cross metathesis.

Authors: Arnab K Chatterjee; Tae-Lim Choi; Daniel P Sanders; Robert H Grubbs
Journal: J Am Chem Soc Date: 2003-09-17 Impact factor: 15.419

10 in total

9 in total

9. A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.

Authors: Aleksandr Grisin; P Andrew Evans
Journal: Chem Sci Date: 2015-08-06 Impact factor: 9.825

9 in total

Synthesis of the C1-C52 fragment of amphidinol 3, featuring a beta-alkoxy alkyllithium addition reaction.

1. Chemoselective cross-metathesis reaction. Application to the synthesis of the C1-C14 fragment of amphidinol 3.

2. A C-glycosidation approach to the central core of amphidinol 3: synthesis of the c39-c52 fragment.

3. The polyol domain of amphidinol 3. A stereoselective synthesis of the entire C(1)-C(30) sector.

4. Development of an access route to the c31-c52 central core of amphidinol 3.

5. Synthesis of the C31-C67 fragment of amphidinol 3.

Review 6. Catalytic asymmetric organozinc additions to carbonyl compounds.

7. Synthesis of the C(43)-C(67) fragment of amphidinol 3.

8. Synthesis of the C(1)-C(25) fragment of amphidinol 3: application of the double-allylboration reaction for synthesis of 1,5-diols.

9. Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

10. A general model for selectivity in olefin cross metathesis.

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4. Synthesis of the bis-tetrahydropyran core of amphidinol 3.

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9. A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.