A synthetic entry to the tetracyclic ABDE core of akuammiline alkaloids

Anales de Quimica

Volumn 92, Issue 2, 1996, Pages 62-63

  Amat, Mercedes ^a   Hadida, Sabine ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

3 Indolylzinc derivatives; Akuammiline alkaloids; Piperidylindoles; Skeletal rearrangement; Spiroindolenine

Indexed keywords

EID: 33749295498     PISSN: 11302283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Amat M, Hadida S. Bosch J (1994) Tetrahedron Lett 35: 793-796
2. Amat M, Sathyanarayana S. Hadida S, Bosch J (1994) Tetrahedron Lett 35:7123-7126
3. 13C-NMR data of 3-(2-piperidyl)indoles. see Table 1. All yields are from material purified by column chromatography
4. 3). 24.1 (C-6). 28.4 (C-5). 33.0 (C-12). 41.2 (C-4), 43.2 (C-3). 44.8 (C-l). 67.0 (CH.Ar). 111.2 (C-10), 111.7 (C-6a). 118.3 (C-7). 119.1 (C-8). 121.9 (C-9). 126.3 (C-6b). 127.5 (C-/>). 127.8 (C-o). 128.4 (C-m). 135.8 (Clla.C-i/).w). 136.7 (C-lOa). 156.2(C=O)
5. 5a Jackson AH. Smith P (1968) Tetrahedron 24:2227-2239
6. b Rubiralta M, Diez A. Vila C. Bettiol J-L. Troin Y, Sinibaldi M-E (1992) Tetrahedron Lett 33:1233-1236
7. For a review, see: Ungemach F. Cook JM ( 1978) Heterocycles 9: 1089-1119
8. 13C-NMR(75 MHz. CDCI,) & 12.9 (CH,). 26.6 (CH,CH,). 46.8 (C-3'). 49.4 (C-4'). 53.4 and 53.6 (2MeO). 58.3 (CH2N). 60.7 (C-2'). 61.5 (C-5'), 103.3 (OCHO). 111.3 (C-7), 114.6 (C-3). 119.8 (C-4 and C-5), 122.1 (C-6). 122.4 (CH=). 122.9 (CH=). 125.4 (C-3a). 129.5 (C-2), 136.7 (C-7a)
9. For related processes, see: a Wenkert F. Halls TDJ. Kwart LD. Magnusson G. Showalter HDH ( 1981 ) Tetrahedron 37:4017-4025
10. b Kalaus 0. Malkieh N. Katona I, Kajtâr-Peredy M, Koritsânszky T. Kaiman A. Sz.abö L. S/antay C (1985) J Org Chem 50: 3760-3767
11. For precedents, see: a Dolby LJ. Nelson SJ ( 1973) J Org Chem 38:2882-2887
12. b Bennasar M-L. Alvare/ M. Lavilla R. Zulaica E. Bosch J (1990) J Org Chem 55:1156-1168
13. 10a AlvareJ. M. Joule J (1994) In: Saxton JE (ed) Monoterpenoid Indole Alkaloids.
14. In: Taylor EC (ed) The Chemistry of Heterocyclic Compounds. Chichester, Vol 25. Supp] to Part 4. pp 217-259
15. b Bennasar M-L. Zulaica E. Rami'rez A. Bosch J (1996) J Org Chem 61:1239-1251