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Asymmetric Synthesis of (+)‐Aspicilin
Author(s) -
Wang ChunYi,
Hou DuenRen
Publication year - 2012
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.201100587
Subject(s) - chemistry , stereocenter , yield (engineering) , total synthesis , metathesis , stereochemistry , ring closing metathesis , diol , organic chemistry , enantioselective synthesis , catalysis , materials science , polymer , metallurgy , polymerization
Aspicilin ( 1 ), an eighteen membered macrolide with four stereocenters, was synthesized using (3 R ,4 R )‐1,5‐hexadiene‐3,4‐diol and ( S )‐propylene oxide as the starting materials. Sharpless epoxidation on the protected dienediol generated the required three consecutive stereocenters, and malonic ester synthesis added the acetyl unit. Yamaguchi protocol was applied to form the key ester with two terminal olefins ready for the ring‐closing metathesis. RCM, hydrogenation, selenylation, oxidation and deprotections gave aspicilin with 4.7% total yield.