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Literature DB >> 22537293

Total syntheses of anominine and tubingensin A.

Ming Bian¹, Zhen Wang, Xiaochun Xiong, Yu Sun, Carlo Matera, K C Nicolaou, Ang Li.

Abstract

A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6π-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.

Entities: Chemical Gene

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Year: 2012 PMID： 22537293 DOI： 10.1021/ja302765m

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

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Cited

17 in total

1. Total Synthesis of Oridamycins A and B.

Authors: Adam H Trotta
Journal: Org Lett Date: 2015-06-12 Impact factor: 6.005

2. A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

Authors: Wenhan Zhang; Joseph M Ready
Journal: J Am Chem Soc Date: 2016-08-11 Impact factor: 15.419

3. Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.

Authors: Robert J Sharpe; Jeffrey S Johnson
Journal: J Org Chem Date: 2015-10-02 Impact factor: 4.354

4. A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline.

Authors: Robert J Sharpe; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2015-04-09 Impact factor: 15.419

5. Discovery of Unclustered Fungal Indole Diterpene Biosynthetic Pathways through Combinatorial Pathway Reassembly in Engineered Yeast.

Authors: Man-Cheng Tang; Hsiao-Ching Lin; Dehai Li; Yi Zou; Jian Li; Wei Xu; Ralph A Cacho; Maureen E Hillenmeyer; Neil K Garg; Yi Tang
Journal: J Am Chem Soc Date: 2015-10-21 Impact factor: 15.419

6. 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

Total syntheses of anominine and tubingensin A.

1. Total Synthesis of Oridamycins A and B.

2. A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

3. Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.

4. A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline.

5. Discovery of Unclustered Fungal Indole Diterpene Biosynthetic Pathways through Combinatorial Pathway Reassembly in Engineered Yeast.

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

7. Total synthesis of the Daphniphyllum alkaloid daphenylline.

8. Total synthesis of (-)-tubingensin B enabled by the strategic use of an aryne cyclization.

Review 9. Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.

Review 10. Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.