Synthetic studies toward the total synthesis of berkelic acid and lytophilippine A
| dc.contributor.advisor | Hiersemann, Martin | |
| dc.contributor.author | Stiasni, Nikola | |
| dc.contributor.referee | Christmann, Mathias | |
| dc.date.accepted | 2011-02-10 | |
| dc.date.accessioned | 2011-03-08T13:09:19Z | |
| dc.date.available | 2011-03-08T13:09:19Z | |
| dc.date.issued | 2011-03-08 | |
| dc.description.abstract | C16-C20 part of natural product berkelic acid containing two adjacent stereogenic centers has been synthesized employing catalytic asymmetric Gosteli-Claisen rearrangement of 2 alkoxycarbonyl-substituted allyl vinyl ether as a key step. Synthetic sequence leading to the both fragments included 11 linear steps and afforded final products in good to excellent diastereoselectivity and good enantioselectivity. Model study exploring Oxa-Pictet-Spengler condensation as a key coupling step toward the tetracyclic core of berkelic acid has been successfully accomplished. C20-C27 fragment of lytophilippine A has been synthesized in a sequence of 13 linear steps, and in total yield of 8.4%. The synthesis commenced with readily available natural (+) L ascorbic acid and features Evans asymmetric alkylation and asymmetric aldol condensation with norephedrine-derived auxiliary as key steps to install the required C21-C23 anti, syn stereotriad. | en |
| dc.identifier.uri | http://hdl.handle.net/2003/27643 | |
| dc.identifier.uri | http://dx.doi.org/10.17877/DE290R-8830 | |
| dc.language.iso | en | de |
| dc.subject | Berkelic acid | en |
| dc.subject | Lytophilippine A | de |
| dc.subject.ddc | 540 | |
| dc.title | Synthetic studies toward the total synthesis of berkelic acid and lytophilippine A | en |
| dc.type | Text | de |
| dc.type.publicationtype | doctoralThesis | de |
| dcterms.accessRights | open access |