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Synfacts 2010(11): 1218-1218  
DOI: 10.1055/s-0030-1258716
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Cryptoacetalide

Contributor(s):Steven V. Ley, James R. Frost
Y. Zou, A. Deiters*
North Carolina State University, Raleigh, USA
Total Synthesis of Cryptoacetalide
J. Org. Chem.  2010,  75:  5355-5358  
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Further Information

Publication History

Publication Date:
21 October 2010 (online)

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Key words

[2+2+2] cyclotrimerization - spiroketalization - ruthenium catalysis

Significance

Cryptoacetalide and epi-crypto­acetalide were isolated from the root of Salvia ­miltiorrhiza, a common treatment for various diseases in Chinese medicine. They were isolated as an inseparable mixture of cryptoacetalide and epi-cryptoacetalide in a ratio of 3:1.

Comment

The key step involves the cyclotrimerization of alkyne precursor D using Cp*Ru(cod)Cl, proceeding through putative intermediates E and F to give tetrasubstituted arene G. The natural products were completed following PMB deprotection and a photo-induced oxidative spiroketalization to afford cryptoacetalide and epi-cryptacet-alide in a 2:1 ratio.

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