Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

Yasuki Soda; Yasukazu Sugiyama; Makoto Yoritate; Hayato Tajima; Kana Shibuya; Chisato Ogihara; Takeshi Oishi; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.0c02697

Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

Yasuki Soda, Yasukazu Sugiyama, Makoto Yoritate, Hayato Tajima, Kana Shibuya, Chisato Ogihara, Takeshi Oishi, Takaaki Sato, Noritaka Chida

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

28 被引用数 (Scopus)

抄録

The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.

本文言語	英語
ページ（範囲）	7502-7507
ページ数	6
ジャーナル	Organic letters
巻	22
号	19
DOI	https://doi.org/10.1021/acs.orglett.0c02697
出版ステータス	出版済み - 10月 2 2020
外部発表	はい

!!!All Science Journal Classification (ASJC) codes

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.0c02697

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abstract = "The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.",

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AU - Soda, Yasuki

AU - Sugiyama, Yasukazu

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AU - Tajima, Hayato

AU - Shibuya, Kana

AU - Ogihara, Chisato

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2020/10/2

Y1 - 2020/10/2

N2 - The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.

AB - The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.

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Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

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!!!All Science Journal Classification (ASJC) codes

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