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

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

27 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7502-7507
Number of pages	6
Journal	Organic letters
Volume	22
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.0c02697
Publication status	Published - Oct 2 2020
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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

AU - Yoritate, Makoto

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

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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

Abstract

All Science Journal Classification (ASJC) codes

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