A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

Susumi Hatakeyama; Masashi Yoshida; Tomoyuki Esumi; Yoshiharu Iwabuchi; Hiroshi Irie; Toshiki Kawamoto; Hidetoshi Yamada; Mugio Nishizawa

doi:10.1016/S0040-4039(97)10077-6

A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

Susumi Hatakeyama, Masashi Yoshida, Tomoyuki Esumi, Yoshiharu Iwabuchi, Hiroshi Irie, Toshiki Kawamoto, Hidetoshi Yamada, Mugio Nishizawa

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

32 Citations (Scopus)

Abstract

A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl₄ catalyzed addition of 1- trimethylsilylbuta-2,3-diene to an aldehyde and Et₂AICI catalysed cyclization of an epoxytrichloroacetimidate for the construction of its α- substituted serine structure having three contiguous asymmetric centers.

Original language	English
Pages (from-to)	7887-7890
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(97)10077-6
Publication status	Published - 1997 Nov 10
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl4 catalyzed addition of 1- trimethylsilylbuta-2,3-diene to an aldehyde and Et2AICI catalysed cyclization of an epoxytrichloroacetimidate for the construction of its α- substituted serine structure having three contiguous asymmetric centers.",

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T1 - A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

AU - Hatakeyama, Susumi

AU - Yoshida, Masashi

AU - Esumi, Tomoyuki

AU - Iwabuchi, Yoshiharu

AU - Irie, Hiroshi

AU - Kawamoto, Toshiki

AU - Yamada, Hidetoshi

AU - Nishizawa, Mugio

PY - 1997/11/10

Y1 - 1997/11/10

N2 - A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl4 catalyzed addition of 1- trimethylsilylbuta-2,3-diene to an aldehyde and Et2AICI catalysed cyclization of an epoxytrichloroacetimidate for the construction of its α- substituted serine structure having three contiguous asymmetric centers.

AB - A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl4 catalyzed addition of 1- trimethylsilylbuta-2,3-diene to an aldehyde and Et2AICI catalysed cyclization of an epoxytrichloroacetimidate for the construction of its α- substituted serine structure having three contiguous asymmetric centers.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

Abstract

ASJC Scopus subject areas

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