Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues

Haruhiko Fuwa; Yumiko Okamura; Yuichi Morohashi; Taisuke Tomita; Takeshi Iwatsubo; Toshiyuki Kan; Tohru Fukuyama; Hideaki Natsugari

doi:10.1016/j.tetlet.2004.01.087

Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues

Haruhiko Fuwa, Yumiko Okamura, Yuichi Morohashi, Taisuke Tomita, Takeshi Iwatsubo, Toshiyuki Kan, Tohru Fukuyama, Hideaki Natsugari

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

46 Citations (Scopus)

Abstract

A highly efficient method for the synthesis of medium-sized lactams based on intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester has been developed. A variety of 7-10 membered lactams were synthesized in excellent yields. Application of the method to the synthesis of analogues of a potent γ-secretase inhibitor LY411575 and their biological evaluation are also described.

Original language	English
Pages (from-to)	2323-2326
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2004.01.087
Publication status	Published - 2004 Feb 8

Keywords

Aza-Wittig reaction
Medium-sized lactams
Staudinger reaction
Structure-activity relationship
γ-Secretase inhibitor

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.01.087

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Fuwa, H., Okamura, Y., Morohashi, Y., Tomita, T., Iwatsubo, T., Kan, T., Fukuyama, T., & Natsugari, H. (2004). Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues. Tetrahedron Letters, 45(11), 2323-2326. https://doi.org/10.1016/j.tetlet.2004.01.087

Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester : Synthesis and biological evaluation of LY411575 analogues. / Fuwa, Haruhiko; Okamura, Yumiko; Morohashi, Yuichi; Tomita, Taisuke; Iwatsubo, Takeshi; Kan, Toshiyuki; Fukuyama, Tohru; Natsugari, Hideaki.

In: Tetrahedron Letters, Vol. 45, No. 11, 08.02.2004, p. 2323-2326.

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

Fuwa, H, Okamura, Y, Morohashi, Y, Tomita, T, Iwatsubo, T, Kan, T, Fukuyama, T & Natsugari, H 2004, 'Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues', Tetrahedron Letters, vol. 45, no. 11, pp. 2323-2326. https://doi.org/10.1016/j.tetlet.2004.01.087

Fuwa, Haruhiko ; Okamura, Yumiko ; Morohashi, Yuichi ; Tomita, Taisuke ; Iwatsubo, Takeshi ; Kan, Toshiyuki ; Fukuyama, Tohru ; Natsugari, Hideaki. / Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester : Synthesis and biological evaluation of LY411575 analogues. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 11. pp. 2323-2326.

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title = "Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues",

abstract = "A highly efficient method for the synthesis of medium-sized lactams based on intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester has been developed. A variety of 7-10 membered lactams were synthesized in excellent yields. Application of the method to the synthesis of analogues of a potent γ-secretase inhibitor LY411575 and their biological evaluation are also described.",

keywords = "Aza-Wittig reaction, Medium-sized lactams, Staudinger reaction, Structure-activity relationship, γ-Secretase inhibitor",

author = "Haruhiko Fuwa and Yumiko Okamura and Yuichi Morohashi and Taisuke Tomita and Takeshi Iwatsubo and Toshiyuki Kan and Tohru Fukuyama and Hideaki Natsugari",

note = "Funding Information: This work was financially supported in part by a Grant for the 21st Century COE Program from Ministry of Education, Culture, Sports, Science and Technology (MEXT). Continuous support by Takeda Chemical Industries, Ltd is gratefully acknowledged.",

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AU - Fuwa, Haruhiko

AU - Okamura, Yumiko

AU - Morohashi, Yuichi

AU - Tomita, Taisuke

AU - Iwatsubo, Takeshi

AU - Kan, Toshiyuki

AU - Fukuyama, Tohru

AU - Natsugari, Hideaki

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Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues

Abstract

Keywords

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