Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination

Takehiko Yoshimitsu; Tatsunori Ino; Naoyuki Futamura; Takuma Kamon; Tetsuaki Tanaka

doi:10.1021/ol9012684

Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination

Takehiko Yoshimitsu, Tatsunori Ino, Naoyuki Futamura, Takuma Kamon, Tetsuaki Tanaka

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

The second-generation approach to (-)-agelastatin A has been established. The present strategy features the FeBr₂-mediated radical cyclization of 2-cyclopentenyloxycarbonyl azide that allows for the stereoselective installation of a cis-vicinal aminobromo functionality suitable for producing the BCD-ring system of agelastatin A. The aminobromination method streamlines access to oxazolidinone, a key intermediate in the previously reported synthesis, thereby culminating in the new total synthesis of (-)-agelastatin A.

Original language	English
Pages (from-to)	3402-3405
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	15
DOIs	https://doi.org/10.1021/ol9012684
Publication status	Published - Aug 6 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9012684

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AU - Ino, Tatsunori

AU - Futamura, Naoyuki

AU - Kamon, Takuma

AU - Tanaka, Tetsuaki

PY - 2009/8/6

Y1 - 2009/8/6

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AB - The second-generation approach to (-)-agelastatin A has been established. The present strategy features the FeBr2-mediated radical cyclization of 2-cyclopentenyloxycarbonyl azide that allows for the stereoselective installation of a cis-vicinal aminobromo functionality suitable for producing the BCD-ring system of agelastatin A. The aminobromination method streamlines access to oxazolidinone, a key intermediate in the previously reported synthesis, thereby culminating in the new total synthesis of (-)-agelastatin A.

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Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination

Abstract

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