Iridoids from Carbohydrates via Pauson−Khand Reaction: Synthesis of Advanced Highly Oxygenated Cyclopentane-Annulated Pyranosides from d-Glucal Derivatives
- 1 October 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 64 (22) , 8302-8310
- https://doi.org/10.1021/jo991044x
Abstract
The Pauson−Khand reaction on suitable 4-oxa-hept-1-en-6-ynes (1, 17) obtained from 3,4,6-tri-O-acetyl-d-glucal gives the cyclopentane-annulated pyranosides (2, 18) that can be efficiently and stereoselectivelly transformed into chiral, advanced, highly oxygenated intermediates (10, 16, 24) for the synthesis of iridoid aglycones.Keywords
This publication has 28 references indexed in Scilit:
- Carbocycles from Carbohydrates via Free Radical Cyclizations: Synthesis and Manipulation of Annulated FuranosesSynlett, 1998
- THE ASYMMETRIC PAUSON-KHAND REACTION. A REVIEWOrganic Preparations and Procedures International, 1998
- Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidateChemical Communications, 1997
- Palladium−Cobalt-Mediated Double Annulation Process: A New Strategy to Chiral and Polysubstituted Bis-Cyclopentanoids on Carbohydrate PrecursorsThe Journal of Organic Chemistry, 1996
- Asymmetric Pauson−Khand Reaction. Cobalt-Mediated Cycloisomerization of 1,6-Enynes in Carbohydrate Templates: Synthesis of Bis-Heteroannulated PyranosidesThe Journal of Organic Chemistry, 1996
- Iodine-catalyzed Ferrier Reaction 1. A Mild and Highly Versatile Glycosylation of Hydroxyl and Phenolic Groups1Synlett, 1995
- A mutagenic new iridoid in the water extract of catalpae fructus.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- Cyclopentane-annelated pyranosides: a new approach to chiral iridoid synthesisJournal of the Chemical Society, Chemical Communications, 1987
- Total synthesis of loganinJournal of the American Chemical Society, 1970
- Total synthesis of racemic genipinJournal of the American Chemical Society, 1967