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Literature DB >> 21553860

Total synthesis of (±)-aspidophylline A.

Abstract

We report the total synthesis of (±)-aspidophylline A, one of many complex furoindoline-containing alkaloids that has not been synthesized previously. Our route features a number of key transformations, including a Heck cyclization to assemble the [3.3.1]-bicyclic scaffold as well as a late-stage interrupted Fischer indolization to install the furoindoline and construct the natural product's pentacyclic framework.

Entities: Chemical

Mesh：

Substances：
Indole Alkaloids

Year: 2011 PMID： 21553860 DOI： 10.1021/ja203227q

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

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Cited

15 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

Review 2. Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors: Barry M Trost; Maksim Osipov
Journal: Chemistry Date: 2015-09-10 Impact factor: 5.236

3. Total synthesis of (+)-scholarisine A.

Authors: Gregory L Adams; Patrick J Carroll; Amos B Smith
Journal: J Am Chem Soc Date: 2012-01-25 Impact factor: 15.419

4. Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Authors: Jie S Zhu; Jung-Ho Son; Andrew P Teuthorn; Makhluf J Haddadin; Mark J Kurth; Dean J Tantillo
Journal: J Org Chem Date: 2017-09-28 Impact factor: 4.354

5. Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.

Authors: Jesus Moreno; Elias Picazo; Lucas A Morrill; Joel M Smith; Neil K Garg
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

6. Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors: Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal: Synlett Date: 2017 Impact factor: 2.454

Total synthesis of (±)-aspidophylline A.

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

Review 2. Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

3. Total synthesis of (+)-scholarisine A.

4. Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

5. Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.

6. Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

7. Nine-step enantioselective total synthesis of (-)-vincorine.

8. Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

9. Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.

10. Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.