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Literature DB >> 12182569

Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.

Robert E Maleczka¹, Lamont R Terrell, Feng Geng, Joseph S Ward.

Abstract

[structure: see text] A highly convergent synthesis of the proposed structure of amphidinolide A is reported. Instructive applications of several organometallic processes are illustrated, including a highly selective ring-closing metathesis reaction.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 12182569 DOI： 10.1021/ol0262284

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

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Cited

9 in total

1. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors: Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal: J Org Chem Date: 2004-04-02 Impact factor: 4.354

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. 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

Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.

1. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

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

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

4. Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.

5. Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations.

6. Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.

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

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

9. Total Synthesis of Pulvomycin D.