Synthesis of Glycerol Homologues

Abstract

A series of monoprotected glycerol homologues and triols were prepared in high overall yields (>90%) via the hydroboration–oxidation of the corresponding dienols. Hydroboration with disiamylborane and concomitant alkaline oxidation (NaOH, H₂O₂) was found to be a mild, high-yielding, and highly efficient method for the construction of a variety of glycerol homologues.

Key words

hydroboration - diols - triols - diene - disiamylborane

• References and notes

• 1 Fujita K, Fujii T, Yamaguchi R. Org. Lett. 2004; 6: 3525
• 2 Miao L, DiMaggio SC, Shu H, Trudell ML. Org. Lett. 2009; 11: 1579
• 3 Kawahara R, Fujita K, Yamaguchi R. J. Am. Chem. Soc. 2010; 132: 15108

For a review of amphibian alkaloids see:
• 4a Daly JW, Spande TF, Garraffo HM. J. Nat. Prod. 2005; 68: 1556
• 4b Daly J. J. Med. Chem. 2003; 46: 445
• 5 Schwartz BD, McErlean CS. P, Fletcher MT, Mazomenos BE, Konstantopoulou MA, Kitching W, De Voss JJ. Org. Lett. 2005; 7: 1173
• 6 Ito M, Osaku A, Shiibashi A, Ikariya T. Org. Lett. 2007; 9: 1821
• 7 Colonge J, Jeltsch P. Bull. Soc. Chim. Fr. 1963; 6: 1296
• 8 Green TW, Wutts PG. M. Protective Groups in Organic Synthesis . 3rd ed. John Wiley & Sons; New York: 1999
• 9a Nicolai S, Waser J. Org. Lett. 2011; 13: 6324
• 9b Brown HC, Negishi E, Dickason WC. J. Org. Chem. 1985; 50: 520
• 10a Chiruta C, Jachak S, Clive DL. J. Tetrahedron Lett. 2007; 48: 3141
• 10b Iseki K, Mizuno S, Kuroki Y, Kobayashi Y. Tetrahedron 1999; 55: 977
• 11 For a review of hydroboration chemistry see: Smith K, Pelter A. In Comprehensive Organic Synthesis . Vol. 8. Trost BM, Flemming I. Pergamon; Oxford: 1991: 703-732
• 12 Drescher S, Meister A, Blume A, Karlsson G, Algren M, Dobner B. Chem. Eur. J. 2008; 14: 6796