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Synfacts 2011(8): 0809-0809  
DOI: 10.1055/s-0030-1260753
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Solanoeclepin A

Contributor(s):Steven V. Ley, James R. Frost
K. Tanino*, M. Takahashi, Y. Tomata, H. Tokura, T. Uehara, T. Narabu, M. Miyashita*
Hokkaido University, Sapporo; National Agriculture Research Center for Hokkaido Region, Sapporo and Kogakuin University, Hachioji, Japan
Total Synthesis of Solanoeclepin A
Nat. Chem.  2011,  3:  484-488  
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Publication History

Publication Date:
20 July 2011 (online)

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Key words

solanoeclepin A - Meinwald rearrangement - stereoselective epoxidation - Charette-modified Simmons-Smith cyclopropanation - intramolecular Diels-Alder reaction

Significance

Solanoeclepin A, a complex triterpenoid, was isolated in 1986 by Mulder and co-workers and is a hatch stimulus for the potato cyst nematode, which inflicts considerable damage to crop plants. Cyst nematodes are notoriously hard to exterminate and as such attention has been drawn to study of such stimuli in order to eradicate this problem.

Comment

Key steps in the synthesis include ­several rearrangements and a Charette-modified Simmons-Smith cyclopropanation to complete the key DEFG fragment L. Further elaboration via an intramolecular Diels-Alder reaction completed the ABCDEFG scaffold (N). The first total synthesis of solanoeclepin A was completed in further 16 steps.

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