Total synthesis of (-)-chamobtusin A.

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.

[1]  V. Aggarwal,et al.  Palladium-mediated annulation of vinyl aziridines with Michael acceptors: stereocontrolled synthesis of substituted pyrrolidines and its application in a formal synthesis of (-)-α-kainic acid. , 2011, Angewandte Chemie.

[2]  Hikaru Suzuki,et al.  Total synthesis of (±)-chamobtusin A. , 2011, Chemical communications.

[3]  Hidenori Watanabe,et al.  Synthesis of (±)-chamobtusin A by a presumed biomimetic aza-cyclization. , 2010, Organic letters.

[4]  N. Tan,et al.  Chamobtusin A, a novel skeleton diterpenoid alkaloid from Chamaecyparis obtusa cv. tetragon. , 2007, Organic letters.

[5]  H. Katerinopoulos,et al.  Correction of the structure of a new sesquiterpene from Cistus creticus ssp. creticus. , 2004, Journal of natural products.

[6]  T. Kan,et al.  Ns strategies: a highly versatile synthetic method for amines. , 2004, Chemical communications.

[7]  T. Kan,et al.  Preparation of Secondary Amines From Primary Amines Via 2‐Nitrobenzenesulfonamides: N‐(4‐Methoxybenzyl)‐3‐Phenylpropylamine , 2003 .

[8]  G. Han,et al.  Total syntheses of the Securinega alkaloids (+)-14,15-dihydronorsecurinine, (-)-norsecurinine, and phyllanthine. , 2000, The Journal of organic chemistry.

[9]  Nan-Sheng Li,et al.  Selective hydroboration of terminal alkenes in the presence of aldehydes and ketones , 1997 .

[10]  J. Tsuji,et al.  Palladium-Catalyzed Hydrogenolysis of Allylic and Propargylic Compounds with Various Hydrides , 1996 .

[11]  J. Tsuji,et al.  Stereocontrolled formation of cis and trans ring junctions in hydrindane and decalin systems by palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates , 1992 .

[12]  K. Jørgensen,et al.  A facile oxidation of secondary amines to imines by iodosobenzene or by a terminal oxidant and manganese or iron porphyrins and manganese salen as the catalysts , 1992 .

[13]  P. Müller,et al.  Oxidation of amines to imines with hypervalent iodine , 1988 .

[14]  I. Minami,et al.  Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-Triethylamine , 1986 .

[15]  M. Ihara,et al.  An enantioselective total synthesis of (+)-atisirene by intramolecular double Michael reaction , 1986 .

[16]  J. Freeman.  Less familiar reactions of oximes , 1973 .

[17]  K. Kotera,et al.  Conversion of 2-isoxazolines into aziridines by lithium aluminum hydride reduction , 1970 .

[18]  E. M. Burgess,et al.  The reactions of an N-sulfonylamine inner salt , 1968 .