Stereoselective conversion of l-quebrachitol into a novel hydroxylated caprolactam: Total synthesis of bengamide B

Noritaka Chida; Takahiko Tobe; Katsuyuki Murai; Kaori Yamazaki; Seiichiro Ogawa

doi:10.3987/COM-94-6869

Stereoselective conversion of l-quebrachitol into a novel hydroxylated caprolactam: Total synthesis of bengamide B

Noritaka Chida, Takahiko Tobe, Katsuyuki Murai, Kaori Yamazaki, Seiichiro Ogawa

Department of Applied Chemistry

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

36 Citations (Scopus)

Abstract

The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from l-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.

Original language	English
Pages (from-to)	2383-2388
Number of pages	6
Journal	Heterocycles
Volume	38
Issue number	11
DOIs	https://doi.org/10.3987/COM-94-6869
Publication status	Published - 1994 Nov 1

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-94-6869

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abstract = "The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from l-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.",

author = "Noritaka Chida and Takahiko Tobe and Katsuyuki Murai and Kaori Yamazaki and Seiichiro Ogawa",

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AU - Chida, Noritaka

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AU - Murai, Katsuyuki

AU - Yamazaki, Kaori

AU - Ogawa, Seiichiro

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AB - The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from l-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.

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Stereoselective conversion of l-quebrachitol into a novel hydroxylated caprolactam: Total synthesis of bengamide B

Abstract

ASJC Scopus subject areas

UN SDGs

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