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

Satish Chandra Philkhana; B. Seetharamsingh; Yuvraj B. Dangat; Kumar Vanka; D. Srinivasa Reddy

doi:10.1039/C3CC40541A

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Chemical Communications

Issue 32, 2013

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

Satish Chandra Philkhana,^a B. Seetharamsingh,^a Yuvraj B. Dangat,^b Kumar Vanka^b and D. Srinivasa Reddy*^a

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Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. HomiBhabha Road, Pune, India
E-mail: ds.reddy@ncl.res.in;
Fax: +91 20 25902629 ;
Tel: +91 20 25902445

Division of Physical Chemistry, CSIR-National Chemical Laboratory, Dr. HomiBhabha Road, Pune, India

Chem. Commun., 2013,49, 3342-3344

DOI: 10.1039/C3CC40541A
Received 22 Jan 2013, Accepted 04 Mar 2013
First published online 05 Mar 2013

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Abstract
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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.