Chamobtusin A, a unique diterpene alkaloid isolated from Chamaecyparis obtusa cv. tetragon, is considered to be biosynthesized from an abietane diterpenoid. On the basis of this biosynthetic hypothesis, ferruginol (15) was synthesized from (+)-dehydroabietylamine and then biomimetically transformed into (-)-chamobtusin A in 6 steps (12 steps from (+)-dehydroabietylamine).
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Synthesis of (-)-Chamobtusin A from (+)-Dehydroabietylamine.
J Org Chem
December 2016
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
Chamobtusin A, a unique diterpene alkaloid isolated from Chamaecyparis obtusa cv. tetragon, is considered to be biosynthesized from an abietane diterpenoid. On the basis of this biosynthetic hypothesis, ferruginol (15) was synthesized from (+)-dehydroabietylamine and then biomimetically transformed into (-)-chamobtusin A in 6 steps (12 steps from (+)-dehydroabietylamine).
View Article and Find Full Text PDFTotal synthesis of (-)-chamobtusin A.
Org Lett
December 2012
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
The first asymmetric total synthesis of a structurally unique alkaloid, chamobtusin A (1), is described. The route features a novel aziridine formation from the 1,2-oxazine derivative and a palladium-mediated annulation of the vinylaziridine intermediate.
View Article and Find Full Text PDFTotal synthesis of (±)-chamobtusin A.
Chem Commun (Camb)
July 2011
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
The total synthesis of chamobtusin A, the first diterpenoid alkaloid isolated from the whole Pinales, is described. Key features of the synthesis include a stereoselective intramolecular Michael addition to install a key stereocenter and an oxidative manipulation to prepare a 2H-pyrrole ring.
View Article and Find Full Text PDFSynthesis of (±)-chamobtusin A by a presumed biomimetic aza-cyclization.
Org Lett
November 2010
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
A total synthesis of (±)-chamobtusin A has been accomplished on the basis of our presumed biosynthetic pathway: the imine formation of keto aldehyde followed by intramolecular aza-Michael addition.
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