Application of stereoselective ether transfer to the synthesis of isotactic polyethers.
An efficient, convergent synthetic strategy has been developed which enables the synthesis of a series of naturally occurring isotactic polymethoxy compounds. Ether transfer followed by a hydride workup enables simultaneous, diastereoselective production of two methoxy centers in a single step. High yields and diastereoselectivity are observed even in stereochemically rich, polyoxygenated systems. Direct generation of bis-methyl ether moieties from methoxymethyl ethers minimizes the need for typical protective group strategies and the use of expensive methyl transfer reagents. Moreover, the simultaneous generation of a terminal primary iodide serves as a coupling partner for the generation of higher order congeners.
Liu
Kai
K
Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
Arico
Joseph W
JW
Taylor
Richard E
RE
D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D008293:Malates / Q000737:chemistry; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004987:Ethers; D008293:Malates; D011108:Polymers; C030298:malic acid