Stereoselective reactions. VIII. Stereochemical requirement for the benzylic oxidation of lignan lactone. A highly selective synthesis of the antitumor lignan lactone steganacin by the oxidation of stegane.
- 1 January 1985
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 33 (2) , 609-617
- https://doi.org/10.1248/cpb.33.609
Abstract
A highly efficient synthesis of the antitumor steganin lignan steganacin (1) was accomplished. Bromination of stegane (7) with N-bromosuccinimide followed by treatment with aqueous tetrahydrofuran afforded steganol (3) in 85% yield. Acetylation of 3 gave 1 in 72% yield. Stegane (7) was also oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in AcOH to give 1 directly in 10% yield. Stereochemical requirements for the benzylic oxidation of dibenzocyclocotadiene liganan lactones are discussed.This publication has 5 references indexed in Scilit:
- Asymmetric total synthesis of natural (-)-and unnatural (+)-steganacinTetrahedron, 1984
- Synthesis of (–)-steganoneJournal of the Chemical Society, Perkin Transactions 1, 1982
- The ambient temperature Ullmann reaction and its application to the total synthesis of (.+-.)-steganacinJournal of the American Chemical Society, 1980
- Dibenzocyclooctadiene antileukemic lignan synthesis. (.+-.)-SteganoneThe Journal of Organic Chemistry, 1978
- Synthetic studies on lignan lactones: aryl dithiane route to (.+-.)-podorhizol and (.+-.)-isopodophyllotoxone and approaches to the stegane skeletonThe Journal of Organic Chemistry, 1978