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Tandem Ring‐Closing/Cross‐Metathesis Approach for the Synthesis of Synargentolide B and Its Stereoisomers
Author(s) -
Sabitha Gowravaram,
Shankaraiah Kontham,
Yadav Jhillu S.
Publication year - 2013
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.201300434
Subject(s) - chemistry , diastereomer , ring closing metathesis , stereochemistry , metathesis , stereoselectivity , tandem , natural product , salt metathesis reaction , lactone , combinatorial chemistry , organic chemistry , polymerization , materials science , composite material , catalysis , polymer
Abstract The stereoselective syntheses of synargentolide B and its three stereoisomers have been accomplished from L ‐(+)‐ and D ‐(–)‐diethyl tartrates, D ‐ribose, and D ‐mannitol as chiral pool starting materials. The key step was a tandem ring‐closing/cross‐metathesis reaction in which lactone formation and fragment coupling were accomplished in one pot. The spectroscopic data of synthetic product 2c were in agreement with those reported for the natural product. Synargentolide B isolated by Rivett et al. and the compound isolated by Pereda‐Miranda et al. are not diastereomers, but rather they are identical.