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Total Syntheses of D ‐ xylo ‐ and D ‐ arabino ‐Phytosphingosine Based on the Syntheses of Chiral 1,3‐Oxazines
Author(s) -
Mu Yu,
Jin Tian,
Kim GunWoo,
Kim JinSeok,
Kim SungSoo,
Tian YongShou,
Oh ChangYoung,
Ham WonHun
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200064
Subject(s) - chemistry , oxazines , intramolecular force , stereoselectivity , olefin fiber , stereochemistry , metathesis , combinatorial chemistry , intermolecular force , organic chemistry , catalysis , molecule , polymerization , polymer
An efficient, stereocontrolled, and short synthetic method for the preparation D ‐ xylo ‐ and D ‐ arabino ‐phytosphingsine was achieved utilizing chiral oxazines. The key features of this strategy are the stereoselective intramolecular oxazine formation catalyzed by palladium(0) and an intermolecular olefin cross‐metathesis reaction.