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- W2013963003 abstract "Das Pentaspirohenicosanol 6 reagiert mit Thionylchlorid in Pyridin unter fünffacher Cyclobutylmethyl-Cyclopentyl-Umlagerung zu einem all-cis-anellierten hexacyclischen Olefin 17, dessen Struktur und Konfiguration über eine Kristallstrukturanalyse eines hiervon abgeleiteten Epoxids 18 geklärt wurde. Die Umlagerung ist konformativ kontrolliert und für eine Synthese des [6.5]Coronans (5) geeignet. Der Alkohol 6 wurde aus dem Trion 7 über eine Folge aus selektiver Dicyclopropylidenierung, erschöpfender Epoxydierung, Oxaspiropentan-Cyclobutanon-Umlagerung, selektiver Reduktion und Addition von Methyllithium erhalten (7→8→10→11→12→6). The pentaspirohenicosanol 6 reacts with thionyl chloride in pyridine to give, in a fivefold cyclobutymethyl-cyclopentyl rearrangement, the all-cis annulated hexacyclic olefin 17, whose structure and conformation was established by X-ray analysis of an epoxide 18 derived therefrom. The rearrangement is conformationally controlled and suitable for the synthesis of [6.5]coronane (5). The alcohol 6 was obtained from trione 7 by a sequence of selective dicyclopropylidenation, exhaustive epoxidation, oxaspiropentane to cyclobutanone rearrangement, selective reduction and addition of methyllithium (7→8→10→11→12→6)." @default.
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- W2013963003 date "1988-03-01" @default.
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- W2013963003 title "Polyspirane, 14. — Umlagerungskaskaden, 9. Fünffache Cyclobutylmethyl‐Cyclopentyl‐Umlagerung an einem Pentaspiro[3.0.3.0.3.0.3.0.3.1]henicosanol — Eine Schlüsselsequenz zur Synthese des [6.5]Coronans" @default.
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- W2013963003 doi "https://doi.org/10.1002/cber.19881210321" @default.
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