Source:http://linkedlifedata.com/resource/pubmed/id/11572673
Switch to
Predicate | Object |
---|---|
rdf:type | |
lifeskim:mentions | |
pubmed:issue |
39
|
pubmed:dateCreated |
2001-9-26
|
pubmed:abstractText |
A practical stereocontrolled synthesis of (+)-discodermolide (1) has been completed in 10.3% overall yield (23 steps longest linear sequence). The absolute stereochemistry of the C(1)-C(6) (7), C(9)-C(16) (8), and C(17)-C(24) (9) subunits was established via substrate-controlled, boron-mediated, aldol reactions of the chiral ethyl ketones 10, 11, and 12. Key fragment coupling reactions were a lithium-mediated, anti-selective, aldol reaction of aryl ester 8 (under Felkin-Anh induction from the aldehyde component 9), followed by in situ reduction to produce the 1,3-diol 40, and a (+)-diisopinocampheylboron chloride-mediated aldol reaction of methyl ketone 7 (overturning the inherent substrate induction from the aldehyde component 52) to give the (7S)-adduct 58. The flexibility of our overall strategy is illustrated by the synthesis of a number of diastereomers and structural analogues of discodermolide, which should serve as valuable probes for structure-activity studies.
|
pubmed:language |
eng
|
pubmed:journal | |
pubmed:citationSubset |
IM
|
pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/3-hydroxybutanal,
http://linkedlifedata.com/resource/pubmed/chemical/Aldehydes,
http://linkedlifedata.com/resource/pubmed/chemical/Alkanes,
http://linkedlifedata.com/resource/pubmed/chemical/Antineoplastic Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Carbamates,
http://linkedlifedata.com/resource/pubmed/chemical/Immunosuppressive Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Lactones,
http://linkedlifedata.com/resource/pubmed/chemical/Pyrones,
http://linkedlifedata.com/resource/pubmed/chemical/discodermolide
|
pubmed:status |
MEDLINE
|
pubmed:month |
Oct
|
pubmed:issn |
0002-7863
|
pubmed:author | |
pubmed:issnType |
Print
|
pubmed:day |
3
|
pubmed:volume |
123
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
9535-44
|
pubmed:dateRevised |
2006-11-15
|
pubmed:meshHeading |
pubmed-meshheading:11572673-Aldehydes,
pubmed-meshheading:11572673-Alkanes,
pubmed-meshheading:11572673-Antineoplastic Agents,
pubmed-meshheading:11572673-Carbamates,
pubmed-meshheading:11572673-Immunosuppressive Agents,
pubmed-meshheading:11572673-Lactones,
pubmed-meshheading:11572673-Pyrones,
pubmed-meshheading:11572673-Stereoisomerism
|
pubmed:year |
2001
|
pubmed:articleTitle |
A practical synthesis of (+)-discodermolide and analogues: fragment union by complex aldol reactions.
|
pubmed:affiliation |
University Chemical Laboratory, Cambridge University, Lensfield Road, Cambridge CB2 1EW, UK.
|
pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
|