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Literature DB >> 17165709

Total synthesis of amphidinolide E.

Abstract

A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3.Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17165709 PMCID： PMC2538580 DOI： 10.1021/ja066663j

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

17 in total

1. [3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.

Authors: Zhi-Hui Peng; K A Woerpel
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

2. Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: application to the total synthesis of (+/-)-peduncularine.

Authors: Claudia W Roberson; K A Woerpel
Journal: J Am Chem Soc Date: 2002-09-25 Impact factor: 15.419

Review 3. Chemistry of potent anti-cancer compounds, amphidinolides.

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

4. 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

5. Synthesis of the A-B subunit of angelmicin B.

Authors: William T Lambert; William R Roush
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

6. A three-component coupling strategy for tetrahydrofuran synthesis: application of the diisopropyl tartrate modified (E)-gamma-(dimethylphenylsilyl)allylboronate as an alpha,gamma-allyl dianion equivalent.

Authors: G C Micalizio; W R Roush
Journal: Org Lett Date: 2000-02-24 Impact factor: 6.005

7. Absolute stereochemistry of amphidinolide E.

Authors: Takaaki Kubota; Masashi Tsuda; Jun'ichi Kobayashi
Journal: J Org Chem Date: 2002-03-08 Impact factor: 4.354

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

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

9. Synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation.

Authors: Zhi-Hui Peng; K A Woerpel
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

Review 10. Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.

Authors: Jun'ichi Kobayashi; Masashi Tsuda
Journal: Nat Prod Rep Date: 2004-01-07 Impact factor: 13.423

13 in total

1. INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors: Tadeusz F Molinski; Brandon I Morinaka
Journal: Tetrahedron Date: 2012-11-18 Impact factor: 2.457

2. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors: Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal: J Org Chem Date: 2013-02-13 Impact factor: 4.354

3. Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis.

Authors: William A Donaldson; Subhabrata Chaudhury
Journal: European J Org Chem Date: 2009-08

4. Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction.

Authors: Porino Va; William R Roush
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

5. Iridium-catalyzed anti-diastereo- and enantioselective carbonyl (trimethylsilyl)allylation from the alcohol or aldehyde oxidation level.

Authors: Soo Bong Han; Xin Gao; Michael J Krische
Journal: J Am Chem Soc Date: 2010-07-07 Impact factor: 15.419

6. Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors: Ming Chen; William R Roush
Journal: Org Lett Date: 2011-03-16 Impact factor: 6.005

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

Authors: Robert H Bates; J Brad Shotwell; William R Roush
Journal: Org Lett Date: 2008-09-11 Impact factor: 6.005

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

Authors: Porino Va; William R Roush
Journal: Tetrahedron Date: 2007-06-25 Impact factor: 2.457

9. Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors: Ming Chen; William R Roush
Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419

10. 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