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Synthesis 2010(20): 3453-3460  
DOI: 10.1055/s-0030-1258215
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Approaches to the Total Synthesis of (6R,4′S,6′R)-Cryptofolione

Gowravaram Sabitha*, S. Siva Sankara Reddy, D. Vasudeva Reddy, Vangala Bhaskar, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
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Publication History

Received 4 June 2010
Publication Date:
17 August 2010 (online)

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Abstract

Total syntheses of cryptofolione were accomplished by two different routes via a common intermediate that underwent a cross-metathesis (CM) reaction with a vinyl lactone. The intermediate was prepared by coupling of an acyl anion equivalent with a chiral allyl epoxide synthon, or by Prins cyclization of a trans-cinnamaldehyde with a chiral homoallylic alcohol. Goniothalamin was obtained as a cross-metathesis product of the diacetate and vinyl lactone.

Key words

lactones - total synthesis - heterocycles - cyclizations - cryptofolione

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17

Diacetate 20 was prepared from the diol 17 by acetylation (Scheme  [6] ).

Scheme 6