Unified Total Synthesis of Madangamines A, C, and E

Takahiro Suto; Yuta Yanagita; Yoshiyuki Nagashima; Shinsaku Takikawa; Yasuhiro Kurosu; Naoya Matsuo; Takaaki Satou; Noritaka Chida

doi:10.1021/jacs.7b00807

Unified Total Synthesis of Madangamines A, C, and E

Takahiro Suto, Yuta Yanagita, Yoshiyuki Nagashima, Shinsaku Takikawa, Yasuhiro Kurosu, Naoya Matsuo, Takaaki Satou, Noritaka Chida

Department of Applied Chemistry

Research output: Contribution to journal › Article

21 Citations (Scopus)

Abstract

A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.

Original language	English
Pages (from-to)	2952-2955
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	8
DOIs	https://doi.org/10.1021/jacs.7b00807
Publication status	Published - 2017 Mar 1

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

Suto, T., Yanagita, Y., Nagashima, Y., Takikawa, S., Kurosu, Y., Matsuo, N., Satou, T., & Chida, N. (2017). Unified Total Synthesis of Madangamines A, C, and E. Journal of the American Chemical Society, 139(8), 2952-2955. https://doi.org/10.1021/jacs.7b00807

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AU - Kurosu, Yasuhiro

AU - Matsuo, Naoya

AU - Satou, Takaaki

AU - Chida, Noritaka

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10.1021/jacs.7b00807