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Synthesis 2011(19): 3168-3172  
DOI: 10.1055/s-0030-1260190
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone

Jhillu S. Yadav*a, Ragam Nageshwar Raoa, Begari Prem Kumara, Ragam Somaiaha, Kontham Ravindara, Basi V. Subba Reddya, Ahamad Al Khazim Al Ghamdib
a Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
b Engineer Abdullah Bagshan for Bee Research, King Saudi University, Saudi Arabia
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Publication History

Received 30 April 2011
Publication Date:
29 August 2011 (online)

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Abstract

An efficient and concise stereoselective total synthesis of naturally occurring (-)-cis-aerangis lactone and (-)-cis-cognac lactone is described. The Sharpless asymmetric epoxidation of a primary allylic alcohol and TBSOTf-mediated intramolecular hydride transfer of a chiral epoxy alcohol have been successfully utilized for the construction of a key precursor with syn-aldol stereochemistry using a non-aldol pathway.

Key words

lactones - Wittig olefination - Sharpless asymmetric epoxidation - intramolecular hydride transfer - syn-aldol

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