| pubmed-article:18489155 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C0017725 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C0439851 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C0449444 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C2698172 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C1708533 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C1552596 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C1947931 | lld:lifeskim |
| pubmed-article:18489155 | lifeskim:mentions | umls-concept:C2001792 | lld:lifeskim |
| pubmed-article:18489155 | pubmed:issue | 12 | lld:pubmed |
| pubmed-article:18489155 | pubmed:dateCreated | 2008-6-13 | lld:pubmed |
| pubmed-article:18489155 | 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. | lld:pubmed |
| pubmed-article:18489155 | pubmed:language | eng | lld:pubmed |
| pubmed-article:18489155 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18489155 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:18489155 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18489155 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18489155 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18489155 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18489155 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:18489155 | pubmed:month | Jun | lld:pubmed |
| pubmed-article:18489155 | pubmed:issn | 0022-3263 | lld:pubmed |
| pubmed-article:18489155 | pubmed:author | pubmed-author:PaquetteLeo... | lld:pubmed |
| pubmed-article:18489155 | pubmed:author | pubmed-author:PengXiaowenX | lld:pubmed |
| pubmed-article:18489155 | pubmed:author | pubmed-author:YangJiongJ | lld:pubmed |
| pubmed-article:18489155 | pubmed:author | pubmed-author:KangHo-JungHJ | lld:pubmed |
| pubmed-article:18489155 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:18489155 | pubmed:day | 20 | lld:pubmed |
| pubmed-article:18489155 | pubmed:volume | 73 | lld:pubmed |
| pubmed-article:18489155 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:18489155 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:18489155 | pubmed:pagination | 4548-58 | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:meshHeading | pubmed-meshheading:18489155... | lld:pubmed |
| pubmed-article:18489155 | pubmed:year | 2008 | lld:pubmed |
| pubmed-article:18489155 | pubmed:articleTitle | The carbohydrate-sesquiterpene interface. directed synthetic routes to both (+)- and (-)-fomannosin from D-glucose. | lld:pubmed |
| pubmed-article:18489155 | pubmed:affiliation | Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210-1185, USA. paquette@chemistry.ohio-state.edu | lld:pubmed |
| pubmed-article:18489155 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:18489155 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
