TY - JOUR
T1 - Microwave-assisted gold(I) catalyzed pyran ring opening in brevifloralactone
T2 - synthesis of the hawtriwaic acid core
AU - Miranda, Luis D.
AU - Marrero, Joaquín González
AU - Bautista, Elihú
AU - Maldonado, Emma
AU - Ortega, Alfredo
N1 - Funding Information:
J.G.M. is thankful to UNAM for a postdoctoral fellowship. We also thank I. Chavez, R. Patiño, J. Pérez, L. Velasco, H. Rios, N. Zavala, E. Huerta, and A. Peña, for technical support.
PY - 2009/2/11
Y1 - 2009/2/11
N2 - An efficient microwave-assisted Au(I) catalyzed cleavage of the pyran ring of brevifloralactone is described. We report one of the first combination reactions of gold and microwave irradiation. In base to this reaction, nine new ent-clerodane diterpene derivatives have been obtained by partial synthesis from brevifloralactone, a naturally occurring clerodane-type diterpene isolated in large quantities from the aerial part of Salvia breviflora. The clerodane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from natural sources. The structures of these compounds were stablished from their physical and spectroscopic data.
AB - An efficient microwave-assisted Au(I) catalyzed cleavage of the pyran ring of brevifloralactone is described. We report one of the first combination reactions of gold and microwave irradiation. In base to this reaction, nine new ent-clerodane diterpene derivatives have been obtained by partial synthesis from brevifloralactone, a naturally occurring clerodane-type diterpene isolated in large quantities from the aerial part of Salvia breviflora. The clerodane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from natural sources. The structures of these compounds were stablished from their physical and spectroscopic data.
UR - http://www.scopus.com/inward/record.url?scp=57849161864&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2008.11.087
DO - 10.1016/j.tetlet.2008.11.087
M3 - Artículo
SN - 0040-4039
VL - 50
SP - 633
EP - 635
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 6
ER -