An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol

P. Veeraraghavan Ramachandran; Kamlesh J. Padiya; M. Venkat Ram Reddy; Herbert C. Brown

doi:10.1016/j.jfluchem.2004.01.003

An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol

P. Veeraraghavan Ramachandran, Kamlesh J. Padiya, M. Venkat Ram Reddy, Herbert C. Brown

Chemistry & Biochemistry

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

13 Scopus citations

Abstract

A novel synthetic strategy for the total synthesis of fluorinated analog of blastmycinolactol has been developed using α-pinene based alkoxyallylboration, chelation controlled diastereoselective reduction, and a single step lactonization of the 1,4-diol to the γ-lactone as key steps.

Original language	English (US)
Pages (from-to)	579-583
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	125
Issue number	4
DOIs	https://doi.org/10.1016/j.jfluchem.2004.01.003
State	Published - Apr 1 2004

Keywords

Alkoxyallylboration
Anti-alkylation
Chelation controlled diastereoselective reduction
Dicyclohexylborane
Hydroboration
Ley's oxidation
α-Pinene

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10.1016/j.jfluchem.2004.01.003

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title = "An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol",

abstract = "A novel synthetic strategy for the total synthesis of fluorinated analog of blastmycinolactol has been developed using α-pinene based alkoxyallylboration, chelation controlled diastereoselective reduction, and a single step lactonization of the 1,4-diol to the γ-lactone as key steps.",

keywords = "Alkoxyallylboration, Anti-alkylation, Chelation controlled diastereoselective reduction, Dicyclohexylborane, Hydroboration, Ley's oxidation, α-Pinene",

author = "Ramachandran, \{P. Veeraraghavan\} and Padiya, \{Kamlesh J.\} and Reddy, \{M. Venkat Ram\} and Brown, \{Herbert C.\}",

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doi = "10.1016/j.jfluchem.2004.01.003",

language = "English (US)",

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journal = "Journal of Fluorine Chemistry",

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T1 - An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol

AU - Ramachandran, P. Veeraraghavan

AU - Padiya, Kamlesh J.

AU - Reddy, M. Venkat Ram

AU - Brown, Herbert C.

PY - 2004/4/1

Y1 - 2004/4/1

N2 - A novel synthetic strategy for the total synthesis of fluorinated analog of blastmycinolactol has been developed using α-pinene based alkoxyallylboration, chelation controlled diastereoselective reduction, and a single step lactonization of the 1,4-diol to the γ-lactone as key steps.

AB - A novel synthetic strategy for the total synthesis of fluorinated analog of blastmycinolactol has been developed using α-pinene based alkoxyallylboration, chelation controlled diastereoselective reduction, and a single step lactonization of the 1,4-diol to the γ-lactone as key steps.

KW - Alkoxyallylboration

KW - Anti-alkylation

KW - Chelation controlled diastereoselective reduction

KW - Dicyclohexylborane

KW - Hydroboration

KW - Ley's oxidation

KW - α-Pinene

UR - https://www.scopus.com/pages/publications/2342587342

UR - https://www.scopus.com/inward/citedby.url?scp=2342587342&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2004.01.003

DO - 10.1016/j.jfluchem.2004.01.003

M3 - Article

AN - SCOPUS:2342587342

SN - 0022-1139

VL - 125

SP - 579

EP - 583

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 4

ER -

An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol

Abstract

Keywords

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