Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations

Christopher A. Brown; Varinder K. Aggarwal

doi:10.1002/chem.201503122

Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations

Christopher A. Brown, Varinder K. Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

26 Citations (Scopus)

361 Downloads (Pure)

Abstract

Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 % overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of this synthesis. Rapid complexity: Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 % overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of the synthesis

Original language	English
Pages (from-to)	13900-13903
Number of pages	4
Journal	Chemistry - A European Journal
Volume	21
Issue number	40
DOIs	https://doi.org/10.1002/chem.201503122
Publication status	Published - 1 Sept 2015

Research Groups and Themes

Organic & Biological

Keywords

asymmetric synthesis
boron
iterative homologation
mycolactone
natural products

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10.1002/chem.201503122

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title = "Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations",

abstract = "Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 \% overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of this synthesis. Rapid complexity: Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 \% overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of the synthesis",

keywords = "asymmetric synthesis, boron, iterative homologation, mycolactone, natural products",

author = "Brown, \{Christopher A.\} and Aggarwal, \{Varinder K.\}",

year = "2015",

month = sep,

day = "1",

doi = "10.1002/chem.201503122",

language = "English",

volume = "21",

pages = "13900--13903",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

number = "40",

}

TY - JOUR

T1 - Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations

AU - Brown, Christopher A.

AU - Aggarwal, Varinder K.

PY - 2015/9/1

Y1 - 2015/9/1

N2 - Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 % overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of this synthesis. Rapid complexity: Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 % overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of the synthesis

AB - Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 % overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of this synthesis. Rapid complexity: Using iterative lithiation-borylation homologations, the mycolactone toxin core has been synthesized in 13 steps and 17 % overall yield. The rapid build-up of molecular complexity, high convergence and high stereoselectivity are noteworthy features of the synthesis

KW - asymmetric synthesis

KW - boron

KW - iterative homologation

KW - mycolactone

KW - natural products

UR - https://www.scopus.com/pages/publications/84941809133

U2 - 10.1002/chem.201503122

DO - 10.1002/chem.201503122

M3 - Article (Academic Journal)

C2 - 26332797

AN - SCOPUS:84941809133

SN - 0947-6539

VL - 21

SP - 13900

EP - 13903

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 40

ER -

Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations

Abstract

Research Groups and Themes

Keywords

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3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this

Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this