Journal
CHEMICAL SCIENCE
Volume 3, Issue 8, Pages 2510-2514Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc20468a
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Funding
- NIH [R01GM071779, P41GM081282]
- NSF [CHE-1048804]
- National Center for Research Sources [S10RR025631]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1048804] Funding Source: National Science Foundation
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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.
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