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Synthesis 2011(22): 3706-3710  
DOI: 10.1055/s-0030-1260246
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© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Stereoselective Total Synthesis of (+)-Cryptofolione and the First Synthesis of (-)-Cryptocaryalactone [¹]

P. Balasubramanyam, Gandolla Chinna Reddy, Nayaki Salvanna, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;
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Publication History

Received 1 July 2011
Publication Date:
29 September 2011 (online)

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Abstract

The stereoselective syntheses of the naturally occurring α-pyrone derivatives (+)-cryptofolione and (-)-cryptocaryalactone were efficiently accomplished by using propane-1,3-diol as the starting material. Keck allylation, Mitsunobu center inversion, and olefin cross metathesis were used as the key steps. (-)-Cryptocarya­lactone was synthesized here for the first time.

Key words

total synthesis - lactones - natural products - Keck allylation - Mitsunobu center inversion - olefin cross metathesis

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Part 51 in the series ‘Synthetic Studies on Natural Products’