Total Syntheses of Telisatin A, Telisatin B and Lettowianthine 英文参考文献.docVIP

Molecules 2009, 14, 917-924; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Total Syntheses of Telisatin A, Telisatin B and Lettowianthine Surachai Nimgirawath * and Phansuang Udomputtimekakul Department of Chemistry, Faculty of Science, Silpakorn University; Nakorn Pathom 73000, Thailand; E-mail: Phansuang@ (P.U.) * Author to whom correspondence should be addressed; E-mail: surachai@su.ac.th. Received: 2 February 2009; in revised form: 17 February 2009/ Accepted: 26 February 2009 / Published: 26 February 2009 Abstract: Treatment of 1-(2-bromoarylmethyl)-3,4-dihydroisoquinolines with oxalyl chloride and triethylamine gave 1-(2-bromophenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline- 2,3-dione derivatives, for example, 1-(2-bromophenyl)-5,6-dihydro-8,9- dimethoxypyrrolo[2,1-a]isoquinoline-2,3-dione. Radical cyclisation of these derivatives with tributyltin hydride and 1,1′-azobis(cyclohexanecarbonitrile) afforded telisatin A, telisatin B and lettowianthine. Keywords: Alkaloid; Dioxoaporphine; Isoquinoline; Radical cyclisation; Synthesis. Introduction The telisatin-type aporphine alkaloids form a very small sub-group of the aporphine alkaloids in which N-6 and C-7 are fused to an oxalyl function. To date only five members of this type of aporphine alkaloids have been found to occur in Nature. These are telisatin A (1) and telisatin B (2) from Telitoxicum peruvianum Moldenke (Menispermaceae) [1], lettowianthine (3) and 11-methoxy- lettowianthine (4) from Lettowianthus stellatus Diels (Annonaceae) [2], and laurodionine (5) from Phoebe formosana Hayata (Lauraceae) [3]. Annonbraine, isolated from Annona glaba L (Annonaceae), was also assigned the same structure as lettowianthine (3), although there was a big difference in the melting points of the two alkaloids [4]. The structure of telisatin A was elucidated by comparison of