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Literature DB >> 18783230

Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

Robert H Bates¹, J Brad Shotwell, William R Roush.

Abstract

Stereoselective syntheses of the C(1)-C(9) fragments 18 and 28 of amphidinolide C have been developed. The first-generation sequence involves a diastereoselective chelate-controlled [3 + 2]-annulation reaction of 6 and 7, while the second-generation synthesis involves an intramolecular hetero-Michael cyclization of 8.

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Year: 2008 PMID： 18783230 PMCID： PMC2650083 DOI： 10.1021/ol801852j

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

15 in total

1. Absolute stereochemistry of amphidinolide C.

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

2. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Authors: Jennifer M Tinsley; Eric Mertz; Pek Y Chong; Robert-André F Rarig; William R Roush
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

3. Amphidinolide F, a new cytotoxic macrolide from the marine dinoflagellate Amphidinium sp.

Authors: J Kobayashi; M Tsuda; M Ishibashi; H Shigemori; T Yamasu; H Hirota; T Sasaki
Journal: J Antibiot (Tokyo) Date: 1991-11 Impact factor: 2.649

Review 4. Chemistry of potent anti-cancer compounds, amphidinolides.

Authors: T K Chakraborty; S Das
Journal: Curr Med Chem Anticancer Agents Date: 2001-08

5. Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

Authors: G C Micalizio; W R Roush
Journal: Org Lett Date: 2001-06-14 Impact factor: 6.005

6. [3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins.

Authors: Eric Mertz; Jennifer M Tinsley; William R Roush
Journal: J Org Chem Date: 2005-09-30 Impact factor: 4.354

10. Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.

Authors: Carl V Vogel; Halina Pietraszkiewicz; Omar M Sabry; William H Gerwick; Frederick A Valeriote; Christopher D Vanderwal
Journal: Angew Chem Int Ed Engl Date: 2014-09-12 Impact factor: 15.336

Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

1. Absolute stereochemistry of amphidinolide C.

2. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

3. Amphidinolide F, a new cytotoxic macrolide from the marine dinoflagellate Amphidinium sp.

Review 4. Chemistry of potent anti-cancer compounds, amphidinolides.

5. Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

6. [3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins.

7. Total synthesis of amphidinolide E.

8. Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes.

9. Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

10. Synthesis of the C11-C29 fragment of amphidinolide F.

1. A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

2. Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.

3. Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

4. Total synthesis of stemaphylline N-oxide and related C9a-epimeric analogues.

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

6. Enantioselective total synthesis of amphidinolide F.

7. Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.

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

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

10. Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.