Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

Varinder K. Aggarwal; Liam T. Ball; Simon Carobene; Rickki L. Connelly; Matthew J. Hesse; Benjamin M. Partridge; Philippe Roth; Stephen P. Thomas; Matthew P. Webster

doi:10.1039/c2cc32176a

Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

Varinder K. Aggarwal^*
, Liam T. Ball
, Simon Carobene
, Rickki L. Connelly
, Matthew J. Hesse
, Benjamin M. Partridge
, Philippe Roth
, Stephen P. Thomas
, Matthew P. Webster

^*Corresponding author for this work

School of Chemistry

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

35 Citations (Scopus)

Abstract

The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

Original language	English
Pages (from-to)	9230-9232
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	74
DOIs	https://doi.org/10.1039/c2cc32176a
Publication status	Published - 2012

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Keywords

TERTIARY BORONIC ESTERS
SECONDARY ALCOHOLS
(+)-CURCUPHENOL
(R)-(-)-CURCUPHENOL
(S)-(+)-CURCUPHENOL
(-)-CURCUQUINONE
CONVERSION
ROUTE
PROTODEBORONATION
METHODOLOGY

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@article{3240551d5b394a4eabc8de9e0d7c5e19,

title = "Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes",

abstract = "The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.",

keywords = "TERTIARY BORONIC ESTERS, SECONDARY ALCOHOLS, (+)-CURCUPHENOL, (R)-(-)-CURCUPHENOL, (S)-(+)-CURCUPHENOL, (-)-CURCUQUINONE, CONVERSION, ROUTE, PROTODEBORONATION, METHODOLOGY",

author = "Aggarwal, \{Varinder K.\} and Ball, \{Liam T.\} and Simon Carobene and Connelly, \{Rickki L.\} and Hesse, \{Matthew J.\} and Partridge, \{Benjamin M.\} and Philippe Roth and Thomas, \{Stephen P.\} and Webster, \{Matthew P.\}",

year = "2012",

doi = "10.1039/c2cc32176a",

language = "English",

volume = "48",

pages = "9230--9232",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "74",

}

TY - JOUR

T1 - Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

AU - Aggarwal, Varinder K.

AU - Ball, Liam T.

AU - Carobene, Simon

AU - Connelly, Rickki L.

AU - Hesse, Matthew J.

AU - Partridge, Benjamin M.

AU - Roth, Philippe

AU - Thomas, Stephen P.

AU - Webster, Matthew P.

PY - 2012

Y1 - 2012

N2 - The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

AB - The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

KW - TERTIARY BORONIC ESTERS

KW - SECONDARY ALCOHOLS

KW - (+)-CURCUPHENOL

KW - (R)-(-)-CURCUPHENOL

KW - (S)-(+)-CURCUPHENOL

KW - (-)-CURCUQUINONE

KW - CONVERSION

KW - ROUTE

KW - PROTODEBORONATION

KW - METHODOLOGY

U2 - 10.1039/c2cc32176a

DO - 10.1039/c2cc32176a

M3 - Article (Academic Journal)

C2 - 22609828

SN - 1359-7345

VL - 48

SP - 9230

EP - 9232

JO - Chemical Communications

JF - Chemical Communications

IS - 74

ER -

Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

Abstract

Research Groups and Themes

Keywords

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