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. Author manuscript; available in PMC: 2015 Jul 7.
Published in final edited form as: Medchemcomm. 2013 Dec 17;2013(4):619–630. doi: 10.1039/C2MD20348K

Scheme 2.

Scheme 2

Earliest reported synthesis of (N)-methanocarba-adenosine, from a D-ribonolactone derivative 9.7,9 Reagents and conditions: (a) LiCH2P(O)(OMe)2; (b), (i) NaOMe, MeOH; (ii) CrO3, pyridine; (c) K2CO3, 18-crown-6; (d), (i) NaBH4, CeCl3; (ii) Et2Zn, CH2I2, CH2Cl2; (iii) MsCl, pyridine; (e), (i) adenine, K2CO3, 18-crown-6, DMF; (ii) Pd black, HCOOH, MeOH.