Stereocontrolled Total Synthesis of Hedyotol A

Stereocontrolled Total Synthesis of Hedyotol A

The total synthesis of hedyotol A (1), a natural product isolated from Hedyotis lawsoniae (DC.) Wight et Arn. (Rubiaceae), was accomplished in a highly stereocontrolled manner. Key steps include an l-proline-catalyzed cross-aldol reaction and the biomimetic construction of a furofuran lignan skeleto...

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Veröffentlicht in:Organic letters 2014-04, Vol.16 (7), p.1976-1979
Hauptverfasser: Kawabe, Yusuke, Ishikawa, Ryo, Akao, Yusuke, Yoshida, Atsushi, Inai, Makoto, Asakawa, Tomohiro, Hamashima, Yoshitaka, Kan, Toshiyuki
Format: Artikel
Sprache:eng
Schlagworte:
Benzofurans - chemical synthesis
Benzofurans - chemistry
Benzofurans - isolation & purification
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - isolation & purification
Lignans - chemical synthesis
Lignans - chemistry
Lignans - isolation & purification
Molecular Structure
Proline - analogs & derivatives
Proline - chemistry
Rubiaceae - chemistry
Stereoisomerism
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Zusammenfassung:The total synthesis of hedyotol A (1), a natural product isolated from Hedyotis lawsoniae (DC.) Wight et Arn. (Rubiaceae), was accomplished in a highly stereocontrolled manner. Key steps include an l-proline-catalyzed cross-aldol reaction and the biomimetic construction of a furofuran lignan skeleton through a quinomethide intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500524y