Preparative-scale synthesis of both antipodes of B-γ,γ- dimethylallyldiisopinocampheylborane: Application for the synthesis of C 1-C6 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-C₆ subunit of epothilone

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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 C₁-C₆ subunit of epothilone.

Original language	English (US)
Pages (from-to)	1011-1013
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2003.11.087
State	Published - Jan 26 2004

Keywords

B-Methoxydiisopinocampheylborane
Dimethylallylboration
Epothilone
Prenyl alcohol

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10.1016/j.tetlet.2003.11.087

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Preparative-scale synthesis of both antipodes of B-γ,γ- dimethylallyldiisopinocampheylborane : Application for the synthesis of C ₁-C₆ subunit of epothilone. / Ramachandran, P. Veeraraghavan; Prabhudas, Bodhuri; Chandra, J. Subash et al.

In: Tetrahedron Letters, Vol. 45, No. 5, 26.01.2004, p. 1011-1013.

Research output: Contribution to journal › Article › peer-review

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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 C1-C6 subunit of epothilone.",

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AU - Prabhudas, Bodhuri

AU - Chandra, J. Subash

AU - Reddy, M. Venkat Ram

AU - Brown, Herbert C.

PY - 2004/1/26

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KW - Dimethylallylboration

KW - Epothilone

KW - Prenyl alcohol

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