Total synthesis of the proposed structure of didemnaketal B

Haruhiko Fuwa; Kumiko Sekine; Makoto Sasaki

doi:10.1021/ol4017518

Total synthesis of the proposed structure of didemnaketal B

Haruhiko Fuwa, Kumiko Sekine, Makoto Sasaki

研究成果: Article › 査読

14 被引用数 (Scopus)

抄録

Total synthesis of the proposed structure of didemnaketal B has been accomplished. The C7-C21 spiroacetal domain was synthesized by exploiting our Suzuki-Miyaura coupling/spiroacetalization strategy. The C1-C7 acyclic domain was constructed via an Evans syn-aldol reaction and a vinylogous Mukaiyama aldol reaction. Finally, the C22-C28 side chain was introduced by means of a Nozaki-Hiyama-Kishi reaction. Comparison of the NMR spectroscopic data of our synthetic material with those of the authentic sample revealed that the proposed structure requires stereochemical reassignment.

本文言語	English
ページ（範囲）	3970-3973
ページ数	4
ジャーナル	Organic letters
巻	15
号	15
DOI	https://doi.org/10.1021/ol4017518
出版ステータス	Published - 2013 8月 2

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol4017518

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author = "Haruhiko Fuwa and Kumiko Sekine and Makoto Sasaki",

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doi = "10.1021/ol4017518",

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AU - Sekine, Kumiko

AU - Sasaki, Makoto

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AB - Total synthesis of the proposed structure of didemnaketal B has been accomplished. The C7-C21 spiroacetal domain was synthesized by exploiting our Suzuki-Miyaura coupling/spiroacetalization strategy. The C1-C7 acyclic domain was constructed via an Evans syn-aldol reaction and a vinylogous Mukaiyama aldol reaction. Finally, the C22-C28 side chain was introduced by means of a Nozaki-Hiyama-Kishi reaction. Comparison of the NMR spectroscopic data of our synthetic material with those of the authentic sample revealed that the proposed structure requires stereochemical reassignment.

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Total synthesis of the proposed structure of didemnaketal B

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