Structure Confirmation of Dechlorotrichotoxin A through Stereoselective Total Synthesis

The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10 / mixture of trichotoxin A, was successfully achieved, commencing from the natural monoterpenoid (-)-citronellal. Key steps in the synthesis involved introducing three alkenes and establishing a stereog...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2023-11, Vol.86 (11), p.2585-2591
Main Authors: Bae, Dawon, Nam, Joo-Won, Park, Hyojin, Chaudhary, Prakash, Kim, Jung-Ae, Lee, Hyunji, Jeong, Byeong-Seon
Format: Article
Language:English
Subjects:
alcohols
Alkenes - chemistry
allylation
Animals
Antimicrobial Cationic Peptides
enantioselectivity
Ethanol
Molecular Structure
monoterpenoids
olefin
phosphoric acid
Polyketides
Porifera
spectral analysis
Stereoisomerism
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Summary:The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10 / mixture of trichotoxin A, was successfully achieved, commencing from the natural monoterpenoid (-)-citronellal. Key steps in the synthesis involved introducing three alkenes and establishing a stereogenic secondary alcohol center. These transformations were accomplished through olefin cross-metathesis, Tebbe olefination, and enantioselective allylation using a chiral phosphoric acid. A comparison of the spectroscopic data between the synthetic dechlorotrichotoxin A and the reported spectra confirmed that the polyketide isolated from a species corresponds to trichotoxin A rather than dechlorotrichotoxin A.
ISSN:0163-3864
1520-6025
1520-6025
DOI:10.1021/acs.jnatprod.3c00629