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Literature DB >> 11817951

Biomimetic synthesis of (-)-longithorone A.

Mark E Layton¹, Carl A Morales, Matthew D Shair.

Abstract

An enantioseletive, biomimetic synthesis of (-)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer control during ene-yne metathesis macrocyclizations.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 11817951 DOI： 10.1021/ja016585u

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

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Cited

21 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Total synthesis of (-)-mucocin.

Authors: Michael T Crimmins; Yan Zhang; Frank A Diaz
Journal: Org Lett Date: 2006-05-25 Impact factor: 6.005

3. Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

Authors: Fenghai Guo; Leah C Konkol; Regan J Thomson
Journal: J Am Chem Soc Date: 2010-12-09 Impact factor: 15.419

Review 4. Dearomatization strategies in the synthesis of complex natural products.

Authors: Stéphane P Roche; John A Porco
Journal: Angew Chem Int Ed Engl Date: 2011-04-19 Impact factor: 15.336

Review 5. Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors: Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
Journal: Angew Chem Int Ed Engl Date: 2010 Impact factor: 15.336

10. Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes.

Authors: Yeon-Ju Lee; Richard R Schrock; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-08-05 Impact factor: 15.419

Biomimetic synthesis of (-)-longithorone A.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Total synthesis of (-)-mucocin.

3. Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

Review 4. Dearomatization strategies in the synthesis of complex natural products.

Review 5. Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

6. Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

7. Synthesis of (-)-longithorone A: using organic synthesis to probe a proposed biosynthesis.

8. Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

Review 9. Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

10. Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes.