Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis

Tomoyasu Hirose; Toshiaki Sunazuka; Daisuke Yamamoto; Mutsumi Mouri; Yoshiaki Hagiwara; Takanori Matsumaru; Eisuke Kaji; Satoshi Omura

doi:10.1016/j.tetlet.2006.11.079

Studies toward the total synthesis of irumamycin

stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis

Tomoyasu Hirose, Toshiaki Sunazuka, Daisuke Yamamoto, Mutsumi Mouri, Yoshiaki Hagiwara, Takanori Matsumaru, Eisuke Kaji, Satoshi Omura

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

The basic structure of the C(15)-C(27) part of irumamycin (1) was synthesized. Stereoselective assembly of C16, 17, 22, and an extra C21 stereocenter was achieved by two-directional Brown's asymmetric allyl boration. Group selective PMP acetal formation and oxidative cleavage of vinyl group facilitated the differentiation of the ends of a two-directionally synthesized chain.

Original language	English
Pages (from-to)	413-416
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2006.11.079
Publication status	Published - 2007 Jan 15
Externally published	Yes

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Acetals

irumamycin

C 27

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Hirose, T., Sunazuka, T., Yamamoto, D., Mouri, M., Hagiwara, Y., Matsumaru, T., ... Omura, S. (2007). Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis. Tetrahedron Letters, 48(3), 413-416. https://doi.org/10.1016/j.tetlet.2006.11.079

Studies toward the total synthesis of irumamycin : stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis. / Hirose, Tomoyasu; Sunazuka, Toshiaki; Yamamoto, Daisuke; Mouri, Mutsumi; Hagiwara, Yoshiaki; Matsumaru, Takanori; Kaji, Eisuke; Omura, Satoshi.

In: Tetrahedron Letters, Vol. 48, No. 3, 15.01.2007, p. 413-416.

Research output: Contribution to journal › Article

Hirose, T, Sunazuka, T, Yamamoto, D, Mouri, M, Hagiwara, Y, Matsumaru, T, Kaji, E & Omura, S 2007, 'Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis', Tetrahedron Letters, vol. 48, no. 3, pp. 413-416. https://doi.org/10.1016/j.tetlet.2006.11.079

Hirose T, Sunazuka T, Yamamoto D, Mouri M, Hagiwara Y, Matsumaru T et al. Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis. Tetrahedron Letters. 2007 Jan 15;48(3):413-416. https://doi.org/10.1016/j.tetlet.2006.11.079

Hirose, Tomoyasu ; Sunazuka, Toshiaki ; Yamamoto, Daisuke ; Mouri, Mutsumi ; Hagiwara, Yoshiaki ; Matsumaru, Takanori ; Kaji, Eisuke ; Omura, Satoshi. / Studies toward the total synthesis of irumamycin : stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 3. pp. 413-416.

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10.1016/j.tetlet.2006.11.079