Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1α,25-dihydroxyvitamin D3 CD ring

Kazuo Nagasawa; Naoto Matsuda; Yasuo Noguchi; Masahiro Yamanashi; Yoshiro Zako; Isao Shimizu

Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1α,25-dihydroxyvitamin D₃ CD ring

Kazuo Nagasawa, Naoto Matsuda, Yasuo Noguchi, Masahiro Yamanashi, Yoshiro Zako, Isao Shimizu^*

^*この研究の対応する著者

早稲田大学

研究成果: Article › 査読

4 被引用数 (Scopus)

抄録

A novel chiral synthesis of the CD-ring 2 of 1α,25-dihydroxyvitamin D₃ (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100°C to give enone 16. Reduction of ketone 16 with NaBH₄-CeCl₃ followed by hydrogenation with RhCl-(PPh₃)₃ catalyst gave trans-indanol 32, which was transformed to intermediate 2.

本文言語	English
ページ（範囲）	1483-1490
ページ数	8
ジャーナル	Journal of Organic Chemistry
巻	58
号	6
出版ステータス	Published - 1993

ASJC Scopus subject areas

有機化学

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「Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1α,25-dihydroxyvitamin D₃ CD ring」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

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title = "Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1α,25-dihydroxyvitamin D3 CD ring",

abstract = "A novel chiral synthesis of the CD-ring 2 of 1α,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100°C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.",

author = "Kazuo Nagasawa and Naoto Matsuda and Yasuo Noguchi and Masahiro Yamanashi and Yoshiro Zako and Isao Shimizu",

year = "1993",

language = "English",

volume = "58",

pages = "1483--1490",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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T1 - Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1α,25-dihydroxyvitamin D3 CD ring

AU - Nagasawa, Kazuo

AU - Matsuda, Naoto

AU - Noguchi, Yasuo

AU - Yamanashi, Masahiro

AU - Zako, Yoshiro

AU - Shimizu, Isao

PY - 1993

Y1 - 1993

N2 - A novel chiral synthesis of the CD-ring 2 of 1α,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100°C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

AB - A novel chiral synthesis of the CD-ring 2 of 1α,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100°C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

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