4.4 Article

Stereocontrolled Synthesis of ABC Tricycle of Solanoeclepin A

Journal

SYNLETT
Volume 26, Issue 7, Pages 965-969

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1380399

Keywords

solanoeclepin A; natural products; radical cyclization; iodoetherification; enyne metathesis

Funding

  1. MEXT
  2. Yamada Science Foundation
  3. Daiichi Sankyo Foundation of Life Science
  4. SUNBOR GRANT from the Suntory Institute for Bioorganic Research
  5. Grants-in-Aid for Scientific Research [15K12743, 24580161, 15K07410, 23102015] Funding Source: KAKEN

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A tricyclic compound possessing oxabicyclo[2.2.1]heptane and seven-membered ring of solanoeclepin A, the most active hatching agent of potato cyst nematode, was synthesized from d-pantolactone. The synthesis features a tin-mediated 6-exo-trig radical cyclization followed by iodoetherification and ring-closing enyne metathesis.

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