Stereocontrolled Synthesis of Trichodermatide A

Hard core made easy: The pentacyclic core of trichodermatide A was stereoselectively synthesized from a bis(1,3‐cyclohexanedione) derivative by a ring‐closing reaction followed by an intramolecular ketal formation (see scheme; PPTS=pyridinium p‐toluenesulfonate). The first total synthesis of trichod...

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Veröffentlicht in:	Angewandte Chemie International Edition 2013-03, Vol.52 (13), p.3646-3649
Hauptverfasser:	Shigehisa, Hiroki, Suwa, Yoshihiro, Furiya, Naho, Nakaya, Yuki, Fukushima, Minoru, Ichihashi, Yusuke, Hiroya, Kou
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis cobalt Cobalt - chemistry diastereoselective protection Ethers - chemistry Macrolides - chemical synthesis Macrolides - chemistry natural products polyketides Stereoisomerism total synthesis Trichoderma - chemistry
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Beschreibung
Zusammenfassung:	Hard core made easy: The pentacyclic core of trichodermatide A was stereoselectively synthesized from a bis(1,3‐cyclohexanedione) derivative by a ring‐closing reaction followed by an intramolecular ketal formation (see scheme; PPTS=pyridinium p‐toluenesulfonate). The first total synthesis of trichodermatide A was then completed by the introduction of three hydroxy groups.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201210099