Medium ring ethers by ring expansion-ring contraction: Synthesis of lauthisan

Coster, M. J. and De Voss, J. J. (2002) Medium ring ethers by ring expansion-ring contraction: Synthesis of lauthisan. Organic Letters, 4 18: 3047-3050. doi:10.1021/ol0262946


Author Coster, M. J.
De Voss, J. J.
Title Medium ring ethers by ring expansion-ring contraction: Synthesis of lauthisan
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
Publication date 2002-01-01
Sub-type Article (original research)
DOI 10.1021/ol0262946
Volume 4
Issue 18
Start page 3047
End page 3050
Total pages 4
Place of publication Washington, USA
Publisher American Chemical Society
Language eng
Subject C1
250301 Organic Chemical Synthesis
780103 Chemical sciences
Abstract [GRAPHICS] A new general method for the construction of medium ring ethers has been developed. This involves the ring expansion of halo-O,S-acetals followed by a Ramburg-Backlund ring contraction reaction with concomitant extrusion of the sulfur atom. This methodology has been utilized for the synthesis of cis- and trans-lauthisan.
Keyword Chemistry, Organic
Cis-2-ethyl-8-formyl-3,4,7,8-dihydro-2h-oxocin-3-one 3-ethylene Acetal
8-membered Cyclic Ethers
Enantioselective Synthesis
Brevetoxin-b
(+)-laurencin
Construction
Thionolactones
(+)-lauthisan
Cyclizations
Acetylene
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Chemistry and Molecular Biosciences
 
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Created: Wed, 15 Aug 2007, 03:24:58 EST