Enantioselective construction of biaryl part in the synthesis of stegane related compounds

Hitoshi Abe; Shigemitsu Takeda; Takuro Fujita; Keisuke Nishioka; Yasuo Takeuchi; Takashi Harayama

doi:10.1016/j.tetlet.2004.01.086

Enantioselective construction of biaryl part in the synthesis of stegane related compounds

Hitoshi Abe
, Shigemitsu Takeda
, Takuro Fujita
, Keisuke Nishioka
, Yasuo Takeuchi
, Takashi Harayama

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

43 Citations (Scopus)

Abstract

A Pd-mediated intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives were examined to form benzo[c]chromen-6-ones, and then enantioselective lactone-opening reaction with a borane-oxazaborolidine combination was carried out. The resulting biphenyl was transformed into a key intermediate for the stegane related compounds. The absolute configuration of the biphenyl is also discussed.

Original language	English
Pages (from-to)	2327-2329
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2004.01.086
Publication status	Published - Feb 8 2004
Externally published	Yes

Keywords

Biaryl
Lactone concept
Palladium
Phenyl benzoate
Steganone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.01.086

Cite this

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title = "Enantioselective construction of biaryl part in the synthesis of stegane related compounds",

abstract = "A Pd-mediated intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives were examined to form benzo[c]chromen-6-ones, and then enantioselective lactone-opening reaction with a borane-oxazaborolidine combination was carried out. The resulting biphenyl was transformed into a key intermediate for the stegane related compounds. The absolute configuration of the biphenyl is also discussed.",

keywords = "Biaryl, Lactone concept, Palladium, Phenyl benzoate, Steganone",

author = "Hitoshi Abe and Shigemitsu Takeda and Takuro Fujita and Keisuke Nishioka and Yasuo Takeuchi and Takashi Harayama",

note = "Funding Information: A part of this work was supported by the Japan Society for the Promotion of Science. We also thank the SC-NMR Laboratory of Okayama University for the NMR experiments.",

year = "2004",

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doi = "10.1016/j.tetlet.2004.01.086",

language = "English",

volume = "45",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Enantioselective construction of biaryl part in the synthesis of stegane related compounds

AU - Abe, Hitoshi

AU - Takeda, Shigemitsu

AU - Fujita, Takuro

AU - Nishioka, Keisuke

AU - Takeuchi, Yasuo

AU - Harayama, Takashi

N1 - Funding Information: A part of this work was supported by the Japan Society for the Promotion of Science. We also thank the SC-NMR Laboratory of Okayama University for the NMR experiments.

PY - 2004/2/8

Y1 - 2004/2/8

N2 - A Pd-mediated intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives were examined to form benzo[c]chromen-6-ones, and then enantioselective lactone-opening reaction with a borane-oxazaborolidine combination was carried out. The resulting biphenyl was transformed into a key intermediate for the stegane related compounds. The absolute configuration of the biphenyl is also discussed.

AB - A Pd-mediated intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives were examined to form benzo[c]chromen-6-ones, and then enantioselective lactone-opening reaction with a borane-oxazaborolidine combination was carried out. The resulting biphenyl was transformed into a key intermediate for the stegane related compounds. The absolute configuration of the biphenyl is also discussed.

KW - Biaryl

KW - Lactone concept

KW - Palladium

KW - Phenyl benzoate

KW - Steganone

UR - https://www.scopus.com/pages/publications/1242315565

UR - https://www.scopus.com/pages/publications/1242315565#tab=citedBy

U2 - 10.1016/j.tetlet.2004.01.086

DO - 10.1016/j.tetlet.2004.01.086

M3 - Article

AN - SCOPUS:1242315565

SN - 0040-4039

VL - 45

SP - 2327

EP - 2329

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Enantioselective construction of biaryl part in the synthesis of stegane related compounds

Abstract

Keywords

ASJC Scopus subject areas

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