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Literature DB >> 21028791

Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

Abstract

A convergent synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F is reported. The approach involves the synthesis of the common intermediate tetrahydrofuranyl-β-ketophosphonate via cross metathesis, Pd(0)-catalyzed cyclization, and hydroboration-oxidation. The β-ketophosphonate was coupled to three side chain aldehydes using a Horner-Wadsworth-Emmons (HWE) olefination reaction to give dienones, which were reduced with l-selectride to give the fragments of amphidinolide C and F.

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Year: 2010 PMID： 21028791 PMCID： PMC2981351 DOI： 10.1021/ol102345v

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

26 in total

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Authors: T Kubota; M Tsuda; J Kobayashi
Journal: Org Lett Date: 2001-05-03 Impact factor: 6.005

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Authors: Hyeong-Wook Choi; Katsumasa Nakajima; Damtew Demeke; Fu-An Kang; Hyuk-Sang Jun; Zhao-Kui Wan; Yoshito Kishi
Journal: Org Lett Date: 2002-12-12 Impact factor: 6.005

3. New catalytic cycle for couplings of aldehydes with organochromium reagents.

Authors: Kosuke Namba; Yoshito Kishi
Journal: Org Lett Date: 2004-12-23 Impact factor: 6.005

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Authors: Kosuke Namba; Jiashi Wang; Sheng Cui; Yoshito Kishi
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

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Authors: K C Nicolaou; William E Brenzovich; Paul G Bulger; Tasha M Francis
Journal: Org Biomol Chem Date: 2006-04-26 Impact factor: 3.876

6. Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation.

Authors: Mona A Maalouf; Andrew J Wiemer; Craig H Kuder; Raymond J Hohl; David F Wiemer
Journal: Bioorg Med Chem Date: 2007-01-04 Impact factor: 3.641

7. Copper-catalyzed beta-Boration of alpha,beta-unsaturated carbonyl compounds: rate acceleration by alcohol additives.

Authors: Soungyun Mun; Ji-Eon Lee; Jaesook Yun
Journal: Org Lett Date: 2006-10-12 Impact factor: 6.005

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Authors: James A Marshall; Gregory Schaaf; Andrew Nolting
Journal: Org Lett Date: 2005-11-10 Impact factor: 6.005

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Authors: J Brad Shotwell; William R Roush
Journal: Org Lett Date: 2004-10-14 Impact factor: 6.005

10. Stereoselective synthesis of cyclic ethers via the palladium-catalyzed intramolecular addition of alcohols to phosphono allylic carbonates.

Authors: Anyu He; Nongnuch Sutivisedsak; Christopher D Spilling
Journal: Org Lett Date: 2009-07-16 Impact factor: 6.005

9 in total

1. An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Authors: Sudeshna Roy; Christopher D Spilling
Journal: Org Lett Date: 2012-04-16 Impact factor: 6.005

2. Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization.

Authors: Andrew N Lowell; Matthew D DeMars; Samuel T Slocum; Fengan Yu; Krithika Anand; Joseph A Chemler; Nisha Korakavi; Jennifer K Priessnitz; Sung Ryeol Park; Aaron A Koch; Pamela J Schultz; David H Sherman
Journal: J Am Chem Soc Date: 2017-06-05 Impact factor: 15.419

3. Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

Authors: Sheila Namirembe; Lu Yan; James P Morken
Journal: Org Lett Date: 2020-11-12 Impact factor: 6.005

4. Enantioselective total synthesis of amphidinolide F.

Authors: Subham Mahapatra; Rich G Carter
Journal: Angew Chem Int Ed Engl Date: 2012-07-05 Impact factor: 15.336

5. Convergent Synthesis of the C1-C29 Framework of Amphidinolide F.

Authors: Filippo Romiti; Ludovic Decultot; J Stephen Clark
Journal: J Org Chem Date: 2022-06-08 Impact factor: 4.198

6. Studies for the total synthesis of amphidinolide P.

Authors: David R Williams; Brian J Myers; Liang Mi; Randall J Binder
Journal: J Org Chem Date: 2013-04-26 Impact factor: 4.354

7. Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.

Authors: Nongnuch Sutivisedsak; Surendra Dawadi; Christopher D Spilling
Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415

8. Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

Authors: Subham Mahapatra; Rich G Carter
Journal: J Am Chem Soc Date: 2013-07-11 Impact factor: 15.419

9. Relay cross metathesis reactions of vinylphosphonates.

Authors: Raj K Malla; Jeremy N Ridenour; Christopher D Spilling
Journal: Beilstein J Org Chem Date: 2014-08-19 Impact factor: 2.883

9 in total