Synthetic studies of callyspongiolide: synthesis of the macrolactone core of the molecule

2016 ◽  
Vol 14 (28) ◽  
pp. 6769-6779 ◽  
Author(s):  
Sudhakar Athe ◽  
Ashish Sharma ◽  
Kanakaraju Marumudi ◽  
Subhash Ghosh
Keyword(s):  
Natural Product ◽  
Allylic Alcohol ◽  
Marine Natural Product ◽  
Allylic Alkylation ◽  
Synthetic Studies ◽  
Key Steps

Synthesis of the fully functionalized macrolactone core of the highly cytotoxic marine natural product callyspongiolide has been achievedviaaZ-selective intramolecular H–W–E reaction and allylic alkylation of an activatedZ-allylic alcoholviaan SN2′ fashion as key steps.

Enantioselective total synthesis of (S)-nakinadine B

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 25913-25917 ◽  
Author(s):  
Yuvraj Garg ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Novel Approach ◽  
Key Steps

A novel approach for the synthesis of (S)-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.

Synthetic Studies towards the Marine Natural Product Palmerolide A: Synthesis of the C3-C15 and C16-C23 Fragments

Synlett ◽  
2007 ◽  
Vol 2007 (19) ◽  
pp. 2983-2986
Author(s):  
Christophe Meyer ◽  
Janine Cossy ◽  
Guillaume Cantagrel
Keyword(s):  
Natural Product ◽  
Marine Natural Product ◽  
Synthetic Studies ◽  
Palmerolide A

Synthetic Studies on a Marine Natural Product, Palmerolide A: Synthesis of C1-C9 and C15-C21 Fragments

Synlett ◽  
2007 ◽  
Vol 2007 (10) ◽  
pp. 1537-1540 ◽  
Author(s):  
Krishna Kaliappan ◽  
Parthasarathy Gowrisankar
Keyword(s):  
Natural Product ◽  
Marine Natural Product ◽  
Synthetic Studies ◽  
Palmerolide A

scholarly journals Synthesis of (+)-Darwinolide, a Biofilm-Penetrating Anti-MRSA Agent

2018 ◽  
Author(s):  
Thomas Siemon ◽  
Simon Steinhauer ◽  
Mathias Christmann
Keyword(s):  
Staphylococcus Aureus ◽  
Natural Product ◽  
Claisen Rearrangement ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Marine Natural Product ◽  
Methicillin Resistant ◽  
Key Steps ◽  
The Antarctic

Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was shown to exhibit promising activity against the biofilm phase of methicillin-resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven-membered core with two fused tetrahydrofurans. Here we describe the first synthesis of (+)-darwinolide featuring a convergent aldol fragment coupling, an Ireland-Claisen rearrangement and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm-specific antibiotics.<br>

Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A

2001 ◽  
Vol 79 (11) ◽  
pp. 1562-1592 ◽  
Author(s):  
Oren P Anderson ◽  
Anthony GM Barrett ◽  
Jeremy J Edmunds ◽  
Shun-Ichiro Hachiya ◽  
James A Hendrix ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product ◽  
Aldol Reactions ◽  
Calyculin A ◽  
Coupling Reactions ◽  
Stille Coupling ◽  
Palladium Catalyzed ◽  
Key Steps ◽  
Absolute Stereochemistry

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth–Meyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, Cornforth–Meyers oxazole reaction.

scholarly journals Synthesis of (+)-Darwinolide, a Biofilm-Penetrating Anti-MRSA Agent

2018 ◽  
Author(s):  
Thomas Siemon ◽  
Simon Steinhauer ◽  
Mathias Christmann
Keyword(s):  
Staphylococcus Aureus ◽  
Natural Product ◽  
Claisen Rearrangement ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Marine Natural Product ◽  
Methicillin Resistant ◽  
Key Steps ◽  
The Antarctic

Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was shown to exhibit promising activity against the biofilm phase of methicillin-resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven-membered core with two fused tetrahydrofurans. Here we describe the first synthesis of (+)-darwinolide featuring a convergent aldol fragment coupling, an Ireland-Claisen rearrangement and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm-specific antibiotics.<br>

Synthetic studies toward inducamide C

2021 ◽  
Author(s):  
Ardalan A. Nabi ◽  
Lydia M. Scott ◽  
Daniel P. Furkert ◽  
Jonathan Sperry
Keyword(s):  
Natural Product ◽  
Structural Revision ◽  
Synthetic Studies

The rare benzoxazepine ring in the alkaloid inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary.

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