Linked Life Data

15783214

Source:http://linkedlifedata.com/resource/pubmed/id/15783214

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
12
pubmed:dateCreated
2005-3-23
pubmed:abstractText
The first total synthesis of gymnocin-A (1), a cytotoxic polycyclic ether isolated from a notorious red tide dinoflagellate, Karenia mikimotoi, has been accomplished. The synthesis relies heavily on the Suzuki-Miyaura cross-coupling-based methodology to assemble the tetradecacyclic polyether skeleton. Convergent union of the GHI (5) and KLMN (6) rings, both of which were prepared from a common intermediate 7, and the subsequent ring closure of the J ring delivered the GHIJKLMN ring. The crucial coupling between the ABCD and FGHIJKLMN ring fragments (3 and 4, respectively) and stereoselective installation of the C17 hydroxyl group, followed by cyclization of the E ring gave rise to the tetradecacyclic polyether skeleton 2. Finally, incorporation of the 2-methyl-2-butenal side chain completed the total synthesis of gymnocin-A. The convergent nature of the synthesis, which employs three fragments of comparable complexity, is well-suited for preparation of various structural analogues of gymnocin-A to explore the structure-activity relationship. The results of preliminary structure-activity relationship studies of several synthetic analogues are also provided.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Mar
pubmed:issn
0002-7863
pubmed:author
pubmed:issnType
Print
pubmed:day
30
pubmed:volume
127
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4326-35
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
2005
pubmed:articleTitle
Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues.
pubmed:affiliation
Graduate School of Life Sciences, Tohoku University, Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't