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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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

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, 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

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10.1016/j.tetlet.2006.11.079