A facile method for the solution and solid-phase synthesis of substituted [3.3.1] bicycles.
[reaction: see text] Interest in bicyclic natural products from the Guttiferae classification has led to the development of an improved method for the selenium-mediated cyclization of alkenyl-substituted beta-dicarbonyls (I) to form a variety of bicyclo[3.3.1]nonan-9-ones (II) both in solution and on solid support.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
Pfefferkorn
J A
JA
Cao
G Q
GQ
Kim
S
S
Kessabi
J
J
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D029760:Garcinia / Q000737:chemistry; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D012643:Selenium
D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D012643:Selenium