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

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

* 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.

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Publication details

The article was received on 22 Jan 2013, accepted on 04 Mar 2013 and first published on 05 Mar 2013

Article type: Communication

DOI: 10.1039/C3CC40541A

Citation: 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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Chemical Communications

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

Abstract

Supplementary files

Publication details

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

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