Issue 32, 2013
From the journal:

Chemical Communications

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 Vankab  and  D. Srinivasa Reddy*a  

* Corresponding authors

a 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

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

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.

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

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Article information

DOI
https://doi.org/10.1039/C3CC40541A
Article type
Communication
Submitted
22 Jan 2013
Accepted
04 Mar 2013
First published
05 Mar 2013

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

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

S. C. Philkhana, B. Seetharamsingh, Y. B. Dangat, K. Vanka and D. S. Reddy, Chem. Commun., 2013, 49, 3342 DOI: 10.1039/C3CC40541A

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