(1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol

Description

This sparteine alkaloid was first isolated by Battandier and Malosse from Retama sphaerocarpa Boiss. and found to give colour reactions suggesting a relationship with sparteine. It has [α]²⁰_D + 46.2° (c 1.017, EtOH) and yields crystalline salts and derivatives including the hydrochloride, m.p. 272-3°C; picrate, m.p. 165- 6°C; phenylurethane, m.p. 190-1 °c and the acetyl derivative as hygroscopic crystals, m.p. about 60°C. The earlier structure as 8-hydroxysparteine has been shown to be wrong, the correct structure, established by synthesis, being 12-{3- hydroxysparteine.

References

Battandier, Malosse., Compt. rend., 125, 360,450 (1897)
Ribas, Sanchez, Primo., Anales, [is. y. quim., 42, 516 (1946)
Ribas, Fraga., Anales. Real. Soc. Espan [is. y. QUim., 45B, 1426 (1949)
Ribas, Fraga., ibid, 46B, 665 (1950)
Fragaetal., Tetrahedron, 11,78 (1960)
Revised structure:
Bohlmann et al., Chem. Ber., 98, 653, 659 (1965)
Ribas, Castedo, Garcfa., Tetrahedron Lett., 3181 (1965)
Shin, Fonzes, Marion., Can. 1. Chem., 43,2012 (1965)