Linked Life Data

18489155

Source:http://linkedlifedata.com/resource/pubmed/id/18489155

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
12
pubmed:dateCreated
2008-6-13
pubmed:abstractText
An enantiodivergent strategy for the total chemical synthesis of both naturally occurring (+)-fomannosin (1) and its (-)-antipode (ent-1) from alpha-D-glucose has been developed and successfully implemented. The key steps in the overall pathway include the following: (i) application of the zirconocene-mediated ring contraction of vinyl furanosides for the construction of highly substituted cyclobutanols; (ii) the use of ring-closing metathesis to form the pendant five-membered ring; (iii) making recourse to a monothio malonic ester to allow for chemoselective reduction to sensitive lactone intermediate 45; (iv) hydroxyl-directed dihydroxylation with OsO(4) to generate 48; and (v) sequential elimination via a cyclic sulfite and a cyclobutyl triflate. The bridge between the enantiomeric series consisted of a six-step linkup involving the structural modification of 22 so as to generate ent-30b. Optical activity was fully preserved throughout.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jun
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
20
pubmed:volume
73
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4548-58
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
The carbohydrate-sesquiterpene interface. directed synthetic routes to both (+)- and (-)-fomannosin from D-glucose.
pubmed:affiliation
Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210-1185, USA. paquette@chemistry.ohio-state.edu
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't