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

Chemical communications (Cambridge, England) (2013-03-19)
Satish Chandra Philkhana, B Seetharamsingh, Yuvraj B Dangat, Kumar Vanka, D Srinivasa Reddy
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.

MATERIALS
Product Number
Brand
Product Description

Supelco
(±)-Citronellal, analytical standard
Sigma-Aldrich
(±)-Citronellal, natural, ≥85%, FCC, FG
Sigma-Aldrich
(S)-(−)-Citronellal, 96%
Sigma-Aldrich
(±)-Citronellal, ≥95.0% (GC)