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Efficient Synthesis of the C1‐C9 Fragment of 7,8‐ O ‐Isopropylidene Protected Iriomoteolide 3a Derivative
Author(s) -
Chang ChingYao
Publication year - 2011
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201190054
Subject(s) - chemistry , derivative (finance) , olefin metathesis , moiety , fragment (logic) , stereoselectivity , olefin fiber , metathesis , stereochemistry , tartaric acid , organic chemistry , catalysis , algorithm , polymerization , citric acid , computer science , financial economics , economics , polymer
An efficient and stereoselective synthesis of the C1‐C9 moiety of the 7,8‐ O ‐isopropylidene protected iriomoteolide 3a derivative has been accomplished. In our strategy, we employed olefin cross‐metathesis of the L ‐(+)‐tartaric acid derivative (((4 S ,5 S )‐2,2‐dimethyl‐5‐vinyl‐1,3‐dioxolan‐4‐yl)methoxy)( tert ‐butyl)diphenylsilane with a synthesized methyl ( S )‐3‐methylhex‐5‐enate to successfully provide the correct olefin geometry of the desired fragment.