Synthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans-cis isomerisation of the enamide macrocycle

TitleSynthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans-cis isomerisation of the enamide macrocycle
Publication TypeJournal Article
Year of Publication2013
AuthorsPhilkhana, SChandra, Seetharamsingh, B, Dangat, YB, Vanka, K, D. Reddy, S
JournalChemical Communications
Volume49
Issue32
Pagination3342-3344
Date PublishedMAR
ISSN1359-7345
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.

DOI10.1039/c3cc40541a
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)6.718
Divison category: 
Organic Chemistry
Physical and Materials Chemistry