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

32 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

Fingerprint

inhibitors

synthesis

Oxazolidinones

installing

Azides

Cyclization

rings

agelastatin A

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Yoshimitsu, T., Ino, T., Futamura, N., Kamon, T., & Tanaka, T. (2009). Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination. Organic Letters, 11(15), 3402-3405. https://doi.org/10.1021/ol9012684

Total synthesis of the β-caten in inhibitor, (-)-agelastatin A : A second-generation approach based on radical aminobromination. / Yoshimitsu, Takehiko; Ino, Tatsunori; Futamura, Naoyuki; Kamon, Takuma; Tanaka, Tetsuaki.

In: Organic Letters, Vol. 11, No. 15, 06.08.2009, p. 3402-3405.

Research output: Contribution to journal › Article

Yoshimitsu, T, Ino, T, Futamura, N, Kamon, T & Tanaka, T 2009, 'Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination', Organic Letters, vol. 11, no. 15, pp. 3402-3405. https://doi.org/10.1021/ol9012684

Yoshimitsu T, Ino T, Futamura N, Kamon T, Tanaka T. Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination. Organic Letters. 2009 Aug 6;11(15):3402-3405. https://doi.org/10.1021/ol9012684

Yoshimitsu, Takehiko ; Ino, Tatsunori ; Futamura, Naoyuki ; Kamon, Takuma ; Tanaka, Tetsuaki. / Total synthesis of the β-caten in inhibitor, (-)-agelastatin A : A second-generation approach based on radical aminobromination. In: Organic Letters. 2009 ; Vol. 11, No. 15. pp. 3402-3405.

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10.1021/ol9012684