Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products

2017 ◽  
Vol 19 (9) ◽  
pp. 2140-2144 ◽  
Author(s):  
Hong-Shuang Wang ◽  
Hui-Jing Li ◽  
Jun-Li Wang ◽  
Yan-Chao Wu
Keyword(s):  
Natural Products ◽  
Transition Metals ◽  
Marine Natural Products ◽  
Protecting Groups ◽  
Protecting Group

The atom- and step-economical synthesis of seven puupehenone- and haterumadienone-type marine natural products without the use of protecting groups and transition metals has been achieved from the abundant feedstock chemical sclareolide in only 6 to 9 steps.

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

Synthesis ◽  
2020 ◽  
Author(s):  
Ryan Moreira ◽  
Michael Noden ◽  
Scott D. Taylor
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Total Synthesis ◽  
Cyclic Peptides ◽  
Protecting Groups ◽  
Side Chain ◽  
Coupling Reactions ◽  
Protecting Group

AbstractAzido acids are important synthons for the synthesis of complex peptides. As a protecting group, the azide moiety is atom-efficient, easy to install and can be reduced in the presence of many other protecting groups, making it ideal for the synthesis of branched and/or cyclic peptides. α-Azido acids are less bulky than urethane-protected counterparts and react more effectively in coupling reactions of difficult-to-form peptide and ester bonds. Azido acids can also be used to form azoles on complex intermediates. This review covers the synthesis of azido acids and their application to the total synthesis of complex peptide natural products.1 Introduction2 Synthesis of α-Azido Acids2.1 From α-Amino Acids or Esters2.2 Via α-Substitution2.3 Via Electrophilic Azidation2.4 Via Condensation of N-2-Azidoacetyl-4-Phenylthiazolidin- 2-Thi one Enolates with Aldehydes and Acetals2.5 Synthesis of α,β-Unsaturated α-Azido Acids and Esters3 Synthesis of β-Azido Acids3.1 Preparation of Azidoalanine and 3-Azido-2-aminobutanoic Acids3.2 General Approaches to Preparing β-Azido Acids Other Than Azi doalanine­ and AABA4 Azido Acids in Total Synthesis4.1 α-Azido Acids4.2 β-Azido Acids and Azido Acids Containing an Azide on the Side Chain5 Conclusions

Total synthesis of marine natural products without using protecting groups

Nature ◽  
2007 ◽  
Vol 446 (7134) ◽  
pp. 404-408 ◽  
Author(s):  
Phil S. Baran ◽  
Thomas J. Maimone ◽  
Jeremy M. Richter
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Protecting Groups

scholarly journals Synthesis of Plakortolides E and I Enabled by Base Metal Catalysis

2021 ◽  
Author(s):  
Stefan Leisering ◽  
Alexandros Mavroskoufis ◽  
Patrick Voßnacker ◽  
Reinhold Zimmer ◽  
Mathias Christmann
Keyword(s):  
Natural Products ◽  
Transition Metals ◽  
Base Metal ◽  
Protecting Group ◽  
Efficient Synthesis ◽  
One Pot ◽  
Metal Catalysis ◽  
Bond Forming ◽  
Earth Abundant ◽  
Key Steps

A protecting-group-free synthesis of two endoperoxide natural products, plakortolide E and plakortolide I, is reported. Key-steps feature the use of earth-abundant transition metals, consisting of a vanadium-mediated epoxidation, an iron-catalyzed allylic substitution, and a cobalt-induced endoperoxide formation. Our approach combines redox-economy, chemoselective bond-forming reactions, and telescoping into one-pot operations to forge an overall efficient synthesis.

scholarly journals Aldol Condensations on a 3-Alkylidene-2,5-diketopiperazine: Synthesis of Two Marine Natural Products

Synlett ◽  
2018 ◽  
Vol 29 (10) ◽  
pp. 1303-1306 ◽  
Author(s):  
Magnus Fairhurst ◽  
Muhammad Zeeshan ◽  
Bengt Haug ◽  
Annette Bayer
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Aldol Condensation ◽  
Aromatic Aldehydes ◽  
Protecting Group ◽  
Nmr Analysis ◽  
Phenol Group ◽  
Imidazole Group ◽  
One Step

The synthesis of two marine natural products containing a 3-alkylidene-6-arylidene-2,5-diketopiperazine scaffold by employing two consecutive aldol condensations starting with 1,4-diacetyl-2,5-diketopiperazine is reported. The target compounds contain a phenol or an imidazole group as aryl substituents, respectively, and suitable conditions for the aldol condensation of 1-acyl-3-alkylidene-2,5-diketopiperazine with the required functionalised aromatic aldehydes were developed. Provided the optimal base was used, introduction of the phenol group did not require use of a protecting group. Boc-protection was beneficial for introduction of the imidazole group, and conditions for carrying out the aldol condensation and Boc-deprotection in one step were identified. The stereochemistry of the target compounds was confirmed by NMR analysis.

scholarly journals Synthesis of Plakortolides E and I Enabled by Base Metal Catalysis

2021 ◽  
Author(s):  
Stefan Leisering ◽  
Alexandros Mavroskoufis ◽  
Patrick Voßnacker ◽  
Reinhold Zimmer ◽  
Mathias Christmann
Keyword(s):  
Natural Products ◽  
Transition Metals ◽  
Base Metal ◽  
Protecting Group ◽  
Efficient Synthesis ◽  
One Pot ◽  
Metal Catalysis ◽  
Bond Forming ◽  
Earth Abundant ◽  
Key Steps

A protecting-group-free synthesis of two endoperoxide natural products, plakortolide E and plakortolide I, is reported. Key-steps feature the use of earth-abundant transition metals, consisting of a vanadium-mediated epoxidation, an iron-catalyzed allylic substitution, and a cobalt-induced endoperoxide formation. Our approach combines redox-economy, chemoselective bond-forming reactions, and telescoping into one-pot operations to forge an overall efficient synthesis.

The discoipyrroles: A multifaceted approach to understand a novel family of marine natural products

Planta Medica ◽  
2015 ◽  
Vol 81 (11) ◽  
Author(s):  
DA Colosimo ◽  
F Cai ◽  
Y Hu ◽  
MB Potts ◽  
MA White ◽  
...  
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Multifaceted Approach

Synthesis of Marine Natural Products 1

1992 ◽  
Author(s):  
K. F. Albizati ◽  
V. A. Martin ◽  
M. R. Agharahimi ◽  
D. A. Stolze
Keyword(s):  
Natural Products ◽  
Marine Natural Products
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