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Literature DB >> 10990430

Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction.

Abstract

[reaction: see text]Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TlOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.

Entities: Chemical Disease

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Year: 2000 PMID： 10990430 DOI： 10.1021/ol0062547

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

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Cited

15 in total

1. Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors: Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal: J Org Chem Date: 2011-08-05 Impact factor: 4.354

2. An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors: Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal: Adv Synth Catal Date: 2008-12-18 Impact factor: 5.837

3. Studies toward the synthesis of phomactin A. An approach to the macrocyclic core.

Authors: Dawei Teng; Bo Wang; Alex J Augatis; Nancy I Totah
Journal: Tetrahedron Lett Date: 2007-06-25 Impact factor: 2.415

Review 4. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

10. Intramolecular cyclohexadienone annulations of Fischer carbene complexes: model studies for the synthesis of Phomactins.

Authors: Jie Huang; Huan Wang; Chunrui Wu; William D Wulff
Journal: Org Lett Date: 2007-06-20 Impact factor: 6.005

Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction.

1. Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

2. An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

3. Studies toward the synthesis of phomactin A. An approach to the macrocyclic core.

Review 4. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

5. Synthesis and evaluation of novel analogues of ripostatins.

6. Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.

7. Total synthesis and stereochemical assignment of (-)-ushikulide A.

8. Total synthesis of phomactin A.

9. Studies for the synthesis of xenicane diterpenes. A stereocontrolled total synthesis of 4-hydroxydictyolactone.

10. Intramolecular cyclohexadienone annulations of Fischer carbene complexes: model studies for the synthesis of Phomactins.