Biomimetic total synthesis of the reported structure of (+)-selaginedorffone B

The first enantioselective total synthesis of the reported structure of the structurally unique aromatic tetraterpenoid of anti-cancer potential, (+)-selaginedorffone B ( 2 ), has been accomplished from two modified abietane diterpenoids through an intermolecular Diels-Alder reaction between a bio-i...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2024-09, Vol.15 (36), p.14946-14953
Main Authors: Kundu, Sourav, Jana, Debgopal, Mandal, Nilangshu, Mondal, Ayan, Murmu, Ranjit, Roy, Nanda Kishore, Datta, Ayan, Bisai, Alakesh
Format: Article
Language:English
Subjects:
Alkynes
Biomimetics
Chemical synthesis
Chemistry
Diels-Alder reactions
Enantiomers
Molecular orbitals
NMR
Nuclear magnetic resonance
Stereoselectivity
Two dimensional analysis
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Summary:The first enantioselective total synthesis of the reported structure of the structurally unique aromatic tetraterpenoid of anti-cancer potential, (+)-selaginedorffone B ( 2 ), has been accomplished from two modified abietane diterpenoids through an intermolecular Diels-Alder reaction between a bio-inspired diene 3 (HOMO counterpart) and dienophile 4 (corresponding LUMO counterpart) in a 23-step sequence, whereas the core framework of the monomeric abietane diterpenoid was constructed via alkyne-activated ene-cyclization. Computational analysis was conducted to reveal the intricate regio and diastereoselectivity of this novel Diels-Alder reaction, strengthening the experimental results. The absolute configuration of the synthesized molecule was validated through X-ray studies of late-stage intermediates as well as comprehensive 2D NMR analysis. The first catalytic enantioselective total synthesis of (+)-selaginedorffone B ( 2 ) on a gram scale has been accomplished from two modified abietane diterpenoids, diene 3 and dienophile 4 , through a key intermolecular Diels-Alder reaction.
ISSN:2041-6520
2041-6539
DOI:10.1039/d4sc04103h