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A new approach for the asymmetric total synthesis of umbelactone
Author(s) -
Liu Huawei,
Zhang Tao,
Li Yulin
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20213
Subject(s) - chemistry , stereocenter , total synthesis , stereochemistry , sharpless epoxidation , metathesis , ring closing metathesis , yield (engineering) , lactone , ring (chemistry) , enantioselective synthesis , salt metathesis reaction , organic chemistry , catalysis , polymer , materials science , metallurgy , polymerization
The asymmetric total syntheses of ( R )‐(+)‐ and ( S )‐(–)‐umbelactone were achieved by using the Sharpless asymmetric epoxidation reaction to generate the stereogenic center and a ring‐closing metathesis (RCM) for the formation of the lactone structure. Starting from 3‐methyl‐2‐buten‐1‐ol, the asymmetric total synthesis was achieved in an efficient 6‐step protocol with an overall yield of 16%. Chirality, 2006. © Wiley‐Liss, Inc.
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