NDLI: Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation.

Content Provider	Semantic Scholar
Author	Andrews, Ian P. Kwon, Ohyun
Copyright Year	2012
Abstract	In this study we performed the total synthesis of the terpene indole alkaloid (+)-ibophyllidine through a pathway involving asymmetric phosphine catalysis, with our novel l-4-hydroxyproline-derived chiral phosphine mediating the key [3 + 2] annulation. Hydrogenation of the [3 + 2] adduct allowed the rapid formation of the stereochemically dense pyrrolidine ring of (+)-ibophyllidine in excellent yield with exceptionally high levels of both diastereo- and enantioselectivity. We constructed the remainder of the pentacyclic skeleton through an intramolecular alkylation and an intramolecular aza-Morita-Baylis-Hillman reaction.
Starting Page	2510
Ending Page	2514
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1039/C2SC20468A
PubMed reference number	22798981
Journal	Medline
Volume Number	3
Issue Number	8
Alternate Webpage(s)	http://www.rsc.org/suppdata/sc/c2/c2sc20468a/c2sc20468a.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C2SC20468A
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation.