Synthesis of Glycerol Homologues

Kiran Kumar Thota; Mark L. Trudell

doi:10.1055/s-0033-1339185

Synthesis, Table of Contents

Synthesis 2013; 45(16): 2280-2286
DOI: 10.1055/s-0033-1339185

paper

Synthesis of Glycerol Homologues

Kiran Kumar Thota

Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA Fax: +1(504)2806860 Email: mtrudell@uno.edu

,

Mark L. Trudell*

Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA Fax: +1(504)2806860 Email: mtrudell@uno.edu

› Author Affiliations

Abstract

All articles of this category

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

Full Text

References

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

Supplementary Material

Supporting Information