Abstract
The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S,3R,4aR,9aR)-isomer.
Original language | English (US) |
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Pages (from-to) | 1628-1630 |
Number of pages | 3 |
Journal | Tetrahedron Letters |
Volume | 52 |
Issue number | 14 |
DOIs | |
State | Published - Apr 6 2011 |
Bibliographical note
Funding Information:We thank Dr. John A. Beutler (NCI–Frederick), Dr. Odile Thoisson, and Dr. Françoise Gueritte (ISCN CNRS, Gif-sur-Yvette, France) for sharing data on the activity of (+)-vedelianin in the NCI 60 cell line screen, Dr. John G. Kodet for providing the initial vanillin derivative, and Dr. Nolan R. Mente for providing phosphonate 18 . Financial support in the form of an ACS Division of Medicinal Chemistry predoctoral fellowship (to J.J.T.), a Shriner Fellowship from the University of Iowa (to J.J.T.), from the Roy J. Carver Charitable Trust, and the NIH (R41CA126020 via Terpenoid Therapeutics, Inc.) is gratefully acknowledged.