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Literature DB >> 17298078

Concise, enantioselective total synthesis of (-)-alstonerine.

Abstract

A novel enantioselective total synthesis of (-)-alstonerine has been completed that requires only 15 steps from L-tryptophan. The synthesis features the first application of a Pauson-Khand reaction to synthesize an azabridged bicyclic skeleton. [reaction: see text]

Entities: Chemical

Mesh：

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Year: 2007 PMID： 17298078 PMCID： PMC2516964 DOI： 10.1021/ol0700761

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

21 in total

1. Synthesis of bridged medium-sized rings through the intramolecular Pauson-Khand reaction.

Authors: C J Lovely; H Seshadri; B R Wayland; A W Cordes
Journal: Org Lett Date: 2001-08-09 Impact factor: 6.005

2. Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

Authors: David G Washburn; Richard W Heidebrecht; Stephen F Martin
Journal: Org Lett Date: 2003-09-18 Impact factor: 6.005

3. A Pauson-Khand approach to the synthesis of ingenol.

Authors: Jeffrey D Winkler; Esther C Y Lee; LaToya I Nevels
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

4. Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Authors: Rodrigo B Andrade; Stephen F Martin
Journal: Org Lett Date: 2005-12-08 Impact factor: 6.005

5. [Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions.

Authors: Brandon L Ashfeld; Kenneth A Miller; Anna J Smith; Kristy Tran; Stephen F Martin
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

6. Biomimetic entry to the sarpagan family of indole alkaloids: total synthesis of +-geissoschizine and +-N-methylvellosimine.

Authors: Alexander Deiters; Kevin Chen; C Todd Eary; Stephen F Martin
Journal: J Am Chem Soc Date: 2003-04-16 Impact factor: 15.419

7. The first regiospecific, enantiospecific total synthesis of 6-oxoalstophylline and an improved total synthesis of alstonerine and alstophylline as well as the bisindole alkaloid macralstonine.

Authors: Xuebin Liao; Hao Zhou; Xiangyu Z Wearing; Jun Ma; James M Cook
Journal: Org Lett Date: 2005-08-04 Impact factor: 6.005

8. Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine.

Authors: M Ito; C W Clark; M Mortimore; J B Goh; S F Martin
Journal: J Am Chem Soc Date: 2001-08-22 Impact factor: 15.419

Concise, enantioselective total synthesis of (-)-alstonerine.

1. Synthesis of bridged medium-sized rings through the intramolecular Pauson-Khand reaction.

2. Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

3. A Pauson-Khand approach to the synthesis of ingenol.

4. Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

5. [Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions.

6. Biomimetic entry to the sarpagan family of indole alkaloids: total synthesis of +-geissoschizine and +-N-methylvellosimine.

7. The first regiospecific, enantiospecific total synthesis of 6-oxoalstophylline and an improved total synthesis of alstonerine and alstophylline as well as the bisindole alkaloid macralstonine.

8. Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine.

9. General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.

10. Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

1. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

2. Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

3. Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.

4. Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

5. Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids.