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

研究成果: Article › 査読

6 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	413-416
ページ数	4
ジャーナル	Tetrahedron Letters
巻	48
号	3
DOI	https://doi.org/10.1016/j.tetlet.2006.11.079
出版ステータス	Published - 2007 1 15
外部発表	はい

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

文献へのアクセス

10.1016/j.tetlet.2006.11.079

フィンガープリント「Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

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.

研究成果: Article › 査読

@article{bcfbb0f87ea841fa9f24a981ee647ae2,

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

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.",

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

year = "2007",

month = jan,

day = "15",

doi = "10.1016/j.tetlet.2006.11.079",

language = "English",

volume = "48",

pages = "413--416",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "3",

}

TY - JOUR

T1 - Studies toward the total synthesis of irumamycin

T2 - stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis

AU - Hirose, Tomoyasu

AU - Sunazuka, Toshiaki

AU - Yamamoto, Daisuke

AU - Mouri, Mutsumi

AU - Hagiwara, Yoshiaki

AU - Matsumaru, Takanori

AU - Kaji, Eisuke

AU - Omura, Satoshi

PY - 2007/1/15

Y1 - 2007/1/15

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33845452462&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33845452462&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.11.079

DO - 10.1016/j.tetlet.2006.11.079

M3 - Article

AN - SCOPUS:33845452462

VL - 48

SP - 413

EP - 416

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 3

ER -