Preparative-scale synthesis of both antipodes of B-γ,γ-dimethylallyldiisopinocampheylborane: application for the synthesis of C 1–C 6 subunit of epothilone

P.Veeraraghavan Ramachandran,Bodhuri Prabhudas,J.Subash Chandra,M.Venkat Ram Reddy,Herbert C Brown

doi:10.1016/j.tetlet.2003.11.087

Preparative-scale synthesis of both antipodes of B-γ,γ-dimethylallyldiisopinocampheylborane: application for the synthesis of C 1–C 6 subunit of epothilone

P.Veeraraghavan Ramachandran, Bodhuri Prabhudas + Show 3 more

https://doi.org/10.1016/j.tetlet.2003.11.087

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Journal: Tetrahedron Letters	Publication Date: Dec 10, 2003
Citations: 14

Affiliation: Purdue University West Lafayette

#Prenyl Alcohol #High Enantioselectivities + Show 1 more

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Abstract

A preparative-scale synthesis of B-γ,γ-dimethylallyldiisopinocampheylborane starting from prenyl alcohol has been described. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-dimethylhomoallylic alcohols in high enantioselectivities. The application of this reagent has been demonstrated for the synthesis of C 1–C 6 subunit of epothilone.

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