Synthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans-cis isomerisation of the enamide macrocycle
Title | Synthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans-cis isomerisation of the enamide macrocycle |
Publication Type | Journal Article |
Year of Publication | 2013 |
Authors | Philkhana, SChandra, Seetharamsingh, B, Dangat, YB, Vanka, K, D. Reddy, S |
Journal | Chemical Communications |
Volume | 49 |
Issue | 32 |
Pagination | 3342-3344 |
Date Published | MAR |
ISSN | 1359-7345 |
Abstract | Concise and protecting-group free synthesis of ent-palmyrolide A and (-)-cis-palmyrolide A were achieved starting from commercially available (S)-citronellal. The key fragment of palmyrolide A, ``(5S,7S)-7-hydroxy-5,8,8-trimethylnonanamide'', which makes up the most challenging part of the target molecule, was prepared in just three steps. A plausible mechanism for the trans-cis isomerization of the double bond in the macrocycle has been investigated. |
DOI | 10.1039/c3cc40541a |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 6.718 |
Divison category:
Organic Chemistry
Physical and Materials Chemistry