Multivalent activation in temporary phosphate tethers: a new tether for small molecule synthesis.
[reaction: see text]. A new tether for small molecule synthesis is reported. This functionally active tether mediates the desymmetrization of a pseudo-C(2)-symmetric tris-allylic phosphate triester to generate a P-chiral bicyclo[4.3.1]phosphate containing ample steric and stereoelectronic differentiation for investigating chemo-, regio-, and stereoselective transformations. Overall, the method reported herein demonstrates a fundamentally new role of phosphates in synthesis and provides differentiated polyol building blocks for use in natural product synthesis.
Whitehead
Alan
A
Department of Chemistry, University of Kansas, Lawrence, 66045-7582, USA.
McReynolds
Matthew D
MD
Moore
Joel D
JD
Hanson
Paul R
PR
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D010710:Phosphates; D011108:Polymers; C024617:polyol