Synthesis of the C1–C26 Hexacyclic Subunit of Pectenotoxin 2

Synthesis of the C1–C26 hexacyclic subunit of pectenotoxin-2 (PTX-2) is described that features a stereoselective annulation to generate the C-ring by triple asymmetric Nozaki–Hiyama–Kishi coupling followed by oxidative cyclization. Preparation of the C1–C14 AB spriroketal-containing subunit employs...

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Veröffentlicht in:	Organic letters 2012-11, Vol.14 (22), p.5748-5751
Hauptverfasser:	Kubo, Ozora, Canterbury, Daniel P, Micalizio, Glenn C
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes - chemistry Alkynes - chemistry chemical structure cross-coupling reactions Cyclization Furans - chemical synthesis Furans - chemistry Molecular Structure organic compounds Oxidation-Reduction Pyrans - chemical synthesis Pyrans - chemistry Stereoisomerism stereoselectivity
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Beschreibung
Zusammenfassung:	Synthesis of the C1–C26 hexacyclic subunit of pectenotoxin-2 (PTX-2) is described that features a stereoselective annulation to generate the C-ring by triple asymmetric Nozaki–Hiyama–Kishi coupling followed by oxidative cyclization. Preparation of the C1–C14 AB spriroketal-containing subunit employs a recently developed metallacycle-mediated reductive cross-coupling between a TMS-alkyne and a terminal alkene.
ISSN:	1523-7060 1523-7052 1523-7052
DOI:	10.1021/ol302751b