Diversity Oriented Synthesis of Tricyclic Compounds from Glycals Using the Ferrier and the Pauson−Khand Reactions

Abstract

Diversity oriented synthesis of tricyclic compounds was achieved using a combination of the Ferrier reaction and the Pauson-Khand reaction. Ferrier reaction was effected using NbCl5, and the Pauson-Khand reaction was carried out using Co2(CO)8, acetonitrile-dimethoxyethane. Michael additions using various alkyl, aryl, and heterocyclic thiols were also performed successfully. The Ferrier, Pauson-Khand, and Michael addition reactions were found to be highly diastereoselective.

Novel, Efficient Alkene-Phosphinite Hybrid Ligand Based on d-Glucose

“…This 2,3-unsaturated pyranose can also be prepared from d -glucose ( 8 ) via d -glucal using a Ferrier rearrangement as the key step. Basic deprotection of 9 with subsequent regioselective tritylation led to alcohol 11 . Reaction with diphenyl chlorophosphine under conditions described previously for the preparation of carbohydrate-based oxazoline-phosphinite hybrid ligands yielded the desired hybrid ligand gluco -enoPhos ( 12 ), which was thus obtained in only three steps and good overall yield.…”

Diversity‐Oriented Synthesis of Enantiopure Furofurans from Carbohydrates: An Expedient Approach with Built‐in Michael Acceptor, Masked Aldehyde and Leaving Group in a Single Sugar Derivative

“…Since carbohydrates are inexpensive enantiomerically pure chiral molecules with several contiguous chiral centers,4 it is expected that carbohydrates should be a valuable resource for the synthesis of complex scaffolds. With the notable exception of glycals, which have been used as templates for the synthesis of tricyclic compounds,5a–5c the non‐anomeric carbons of acyclic or cyclic sugar molecules [2d,5d–5f,6] have virtually never been used in the synthetic transformations used for DOS 5,6. In most MCRs and in DOS based on carbohydrates, the terminal anomeric carbon, or a functional group (such as an amine, aldehyde, or carboxylate) attached to the anomeric carbon, participates in the reaction, and the non‐anomeric parts of the acyclic or cyclic sugar molecules remain virtually unused 4,7.…”

A convenient and efficient synthesis of glycals by zinc nanoparticles

“…Recently, the use of glycals in combinatorial chemistry have been studied. 13 To date, numerous efforts have been made to construct glycals, including the reduction of glycosyl halides by metals such as Zn-AcOH, 9 Li-NH 3 , 14 (Cp 2 TiCl) 2 , 15 Cr(II), 16 Zn-MeOHvitamin-B 12 , 17 and Al-Hg 18 or using thiophenyl glycoside, 19 glycosyl sulfones, 20 glycosyl sulfoxides, 21 and electrochemical approaches. 22 However, many of these aforementioned methods have long suffered from a lack of generality because of several drawbacks.…”