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

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
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2003.11.087

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@article{702456150502468d88d034e15346ec27,

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

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.",

author = "Ramachandran, \{P. Veeraraghavan\} and Bodhuri Prabhudas and Chandra, \{J. Subash\} and Reddy, \{M. Venkat Ram\} and Brown, \{Herbert C.\}",

year = "2004",

month = jan,

day = "26",

doi = "10.1016/j.tetlet.2003.11.087",

language = "English (US)",

volume = "45",

pages = "1011--1013",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "5",

}

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

TY - JOUR

T1 - Preparative-scale synthesis of both antipodes of B-γ,γ- dimethylallyldiisopinocampheylborane

T2 - Application for the synthesis of C 1-C6 subunit of epothilone

AU - Ramachandran, P. Veeraraghavan

AU - Prabhudas, Bodhuri

AU - Chandra, J. Subash

AU - Reddy, M. Venkat Ram

AU - Brown, Herbert C.

PY - 2004/1/26

Y1 - 2004/1/26

N2 - 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.

AB - 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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UR - https://www.scopus.com/pages/publications/0347022324#tab=citedBy

U2 - 10.1016/j.tetlet.2003.11.087

DO - 10.1016/j.tetlet.2003.11.087

M3 - Article

AN - SCOPUS:0347022324

SN - 0040-4039

VL - 45

SP - 1011

EP - 1013

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

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

Abstract

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