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Literature DB >> 23802176

Enantioselective synthesis of the 5-6-7 carbocyclic core of the gagunin diterpenoids.

Grant M Shibuya¹, John A Enquist, Brian M Stoltz.

Abstract

A catalytic enantioselective double allylic alkylation reaction has been employed in the synthesis of the core of the gagunin diterpenoids. Enantioenriched material was advanced in 11 steps to afford the core of the highly oxygenated target, which includes two all-carbon quaternary stereocenters.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：
Diterpenes
Oxidants

Year: 2013 PMID： 23802176 PMCID： PMC3743267 DOI： 10.1021/ol401514s

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

15 in total

1. The enantioselective Tsuji allylation.

Authors: Douglas C Behenna; Brian M Stoltz
Journal: J Am Chem Soc Date: 2004-11-24 Impact factor: 15.419

2. Microbial metabolism studies of cyanthiwigin B and synergetic antibiotic effects.

Authors: Jiangnan Peng; Noer Kasanah; Charles E Stanley; Jennifer Chadwick; Frank R Fronczek; Mark T Hamann
Journal: J Nat Prod Date: 2006-05 Impact factor: 4.050

3. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

Authors: John A Enquist; Brian M Stoltz
Journal: Nature Date: 2008-06-26 Impact factor: 49.962

4. Total syntheses of cyanthiwigins B, F, and G.

Authors: John A Enquist; Scott C Virgil; Brian M Stoltz
Journal: Chemistry Date: 2011-07-18 Impact factor: 5.236

5. Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors: Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal: Chemistry Date: 2011-11-14 Impact factor: 5.236

2. Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.

Authors: Zackaria Nairoukh; Gunda G K S Narayana Kumar; Yury Minko; Ilan Marek
Journal: Chem Sci Date: 2016-09-15 Impact factor: 9.825

Review 3. The Allylic Alkylation of Ketone Enolates.

Authors: Lukas Junk; Uli Kazmaier
Journal: ChemistryOpen Date: 2020-09-10 Impact factor: 2.630

3 in total

Enantioselective synthesis of the 5-6-7 carbocyclic core of the gagunin diterpenoids.

1. The enantioselective Tsuji allylation.

2. Microbial metabolism studies of cyanthiwigin B and synergetic antibiotic effects.

3. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

4. Total syntheses of cyanthiwigins B, F, and G.

5. Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

6. A new method for the catalytic aldol reaction to ketones.

7. Polyoxygenated diterpenes from the sponge Phorbas sp.

Review 8. Synthetic efforts toward cyathane diterpenoid natural products.

9. Total syntheses of (+)-echinopine A and B: determination of absolute stereochemistry.

10. α-Diazo-β-ketonitriles: uniquely reactive substrates for arene and alkene cyclopropanation.

1. Late-Stage Diversification: A Motivating Force in Organic Synthesis.

2. Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.

Review 3. The Allylic Alkylation of Ketone Enolates.