The reaction of steroidal 2α-bromo-3-ketones (e.g. 2α-bromocholestan-3-one 2) with ammonia followed by hydrolysis and air-oxidation affords the easily separable mixture of the trans and cis dimeric steroid-pyrazines (3 and 4, respectively).
References
1.
PettitG. R., InoueM., KamanoY., HeraldD. L., ArmC., DufresneC., ChristieN. D., SchmidtJ. M., DoubekD. L., and KrupaT. S., J. Am. Chem. Soc., 1988, 110, 2006.
2.
FukuzawaS., MatsunagaS., and FusetaniN., Tetrahedron, 1995, 51, 6707.
3.
These series of compounds are among the most potent cytostatics ever screened by the National Cancer Institute (USA). For a short review see: GanesanA., Stud. Nat. Prod. Chem., 1996, 18, 875.
4.
LaCourT. G., GuoC., BhandaruS., BoydM. R., and FuchsP. L., J. Am. Chem. Soc., 1998, 120, 692.
5.
GuoC., BhandaruS., and FuchsP. L., J. Am. Chem. Soc., 1996, 118, 10672.
6.
DrögemullerM., FlessnerT., JautelatR., ScholzfU., and WinterfeldtE., Eur. J. Org. Chem., 1998, 2811.
7.
PanY., MerrimanR. L., TanzerL. R., and FuchsP. L., Bioorg. Med. Chem. Lett., 1992, 2, 967.
8.
HeathcockC. H., and SmithS. C., J. Org. Chem., 1994, 59, 6828.
9.
SmithH. E., and HicksA. A., J. Org. Chem., 1971, 36, 3659.
10.
KramerA., UllmannU., and WinterfeldtE., J. Chem. Soc., Perkin Trans. 1, 1993, 2865.
11.
MorzyckiJ. W., GryszkiewiczA., LotowskiZ., and SzczepekW. J., Collect. Czech. Chem. Commun., 1998, 63, 1589.
