Synthetic studies toward penitrem E: enantiocontrolled construction of B-E rings

Enantiocontrolled construction of B-E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnished a tetracyclic product possessing the characteristic cy...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (6), p.1070-1073
Main Authors: Yoshii, Yu, Otsu, Takanori, Hosokawa, Norihiko, Takasu, Kiyosei, Okano, Kentaro, Tokuyama, Hidetoshi
Format: Article
Language:English
Subjects:
Acrylates
Bearing
Chemistry Techniques, Synthetic
Crystallography, X-Ray
Cyclobutane
Ethers
Hydroxyl groups
Molecular Structure
Mycotoxins - chemical synthesis
Mycotoxins - chemistry
Rings (mathematics)
Stereoisomerism
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Summary:Enantiocontrolled construction of B-E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnished a tetracyclic product possessing the characteristic cyclobutane ring bearing a hydroxyl group.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc08505a