| dc.contributor.author |
Cooladouros, EA |
en |
| dc.contributor.author |
Vidali, VP |
en |
| dc.date.accessioned |
2014-06-06T06:46:04Z |
|
| dc.date.available |
2014-06-06T06:46:04Z |
|
| dc.date.issued |
2004 |
en |
| dc.identifier.issn |
09476539 |
en |
| dc.identifier.uri |
http://dx.doi.org/10.1002/chem.200400407 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/2780 |
|
| dc.subject |
Epoxide opening reaction |
en |
| dc.subject |
Natural products |
en |
| dc.subject |
Oxepenes |
en |
| dc.subject |
Ring-closing metathesis |
en |
| dc.subject |
Total synthesis |
en |
| dc.subject.other |
Alcohols |
en |
| dc.subject.other |
Substitution reactions |
en |
| dc.subject.other |
Synthesis (chemical) |
en |
| dc.subject.other |
Epoxide |
en |
| dc.subject.other |
Polycyclic systems |
en |
| dc.subject.other |
Ring-closing metathesis |
en |
| dc.subject.other |
Stereochemistry |
en |
| dc.subject.other |
12 hydroxypalisadin b |
en |
| dc.subject.other |
adociasulfate 2 |
en |
| dc.subject.other |
aplysistatin |
en |
| dc.subject.other |
palisadin a |
en |
| dc.subject.other |
palisadin b |
en |
| dc.subject.other |
sesquiterpenoid |
en |
| dc.subject.other |
toxicol a |
en |
| dc.subject.other |
unclassified drug |
en |
| dc.subject.other |
article |
en |
| dc.subject.other |
asymmetric synthesis |
en |
| dc.subject.other |
drug structure |
en |
| dc.subject.other |
drug synthesis |
en |
| dc.subject.other |
reaction analysis |
en |
| dc.subject.other |
ring closing metathesis |
en |
| dc.subject.other |
stereochemistry |
en |
| dc.subject.other |
structure analysis |
en |
| dc.subject.other |
Cyclization |
en |
| dc.subject.other |
Epoxy Compounds |
en |
| dc.subject.other |
Models, Molecular |
en |
| dc.subject.other |
Molecular Conformation |
en |
| dc.subject.other |
Molecular Structure |
en |
| dc.subject.other |
Oxepins |
en |
| dc.subject.other |
Sesquiterpenes |
en |
| dc.subject.other |
Stereoisomerism |
en |
| dc.subject.other |
Structure-Activity Relationship |
en |
| dc.subject.other |
Sulfuric Acid Esters |
en |
| dc.title |
Novel stereocontrolled approach to syn- and anti-oxepene-cyclogeranyl trans-fused polycyclic systems: Asymmetric total synthesis of (-)-Aplysistatin, (+)-Palisadin A, (+)-Palisadin B, (+)-12-hydroxy-Palisadin B, and the AB ring system of adociasulfate-2 and toxicol A |
en |
| heal.type |
journalArticle |
en |
| heal.identifier.primary |
10.1002/chem.200400407 |
en |
| heal.publicationDate |
2004 |
en |
| heal.abstract |
A new stereocontrolled method for the formation of trans-anti cyclogeranyl-oxepene systems is described. The demanding stereochemistry is secured by stereoselective coupling of a cyclogeranyl tertiary alcohol with a 1,2-unsymmetrically substituted epoxide, while the formation of the highly strained oxepene is achieved employing ring-closing metathesis. Since the stereochemistry of the transfused 6,7-ring system is determined by the epoxide, the method also allows the construction of trans-syn 6,7-ring systems. This approach leads to the synthesis of the AB fragment of Adociasulfate-2 and Toxicol A, for the first time. The flexibility and efficiency of the presented strategy is demonstrated by the total asymmetric synthesis of (-)-Aplysistatin, (+)-Palisadin A, (+)-12-hydroxy-Palisadin B, and (+)-Palisadin B, employing two similar key intermediates. |
en |
| heal.journalName |
Chemistry - A European Journal |
en |
| dc.identifier.issue |
15 |
en |
| dc.identifier.volume |
10 |
en |
| dc.identifier.doi |
10.1002/chem.200400407 |
en |
| dc.identifier.spage |
3822 |
en |
| dc.identifier.epage |
3835 |
en |