Chiral dendralenes for rapid access to enantiomerically pure polycycles

Natalie A. Miller; Anthony C. Willis; Michael N. Paddon-Row; Michael S. Sherburn

doi:10.1002/anie.200603335

Chiral dendralenes for rapid access to enantiomerically pure polycycles

Natalie A. Miller, Anthony C. Willis^*, Michael N. Paddon-Row, Michael S. Sherburn

^*Corresponding author for this work

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

52 Citations (Scopus)

Abstract

(Chemical Equation Presented) On a short fuse: Highly stereoselective and atom-efficient domino Diels-Alder/ lactonization/Diels-Alder sequences can be carried out using simple chiral [3]dendralenes to form fused-ring systems. This short and general approach to cross-conjugated systems promotes the rapid assembly of enantiomerically pure polycyclic ring systems common to biologically interesting terpenoids with virtually complete stereocontrol (see scheme).

Original language	English
Pages (from-to)	937-940
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	6
DOIs	https://doi.org/10.1002/anie.200603335
Publication status	Published - 2007

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abstract = "(Chemical Equation Presented) On a short fuse: Highly stereoselective and atom-efficient domino Diels-Alder/ lactonization/Diels-Alder sequences can be carried out using simple chiral [3]dendralenes to form fused-ring systems. This short and general approach to cross-conjugated systems promotes the rapid assembly of enantiomerically pure polycyclic ring systems common to biologically interesting terpenoids with virtually complete stereocontrol (see scheme).",

keywords = "Cross-coupling, Cycloaddition, Dendralenes, Domino reactions, Fused-ring systems",

author = "Miller, {Natalie A.} and Willis, {Anthony C.} and Paddon-Row, {Michael N.} and Sherburn, {Michael S.}",

year = "2007",

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AU - Willis, Anthony C.

AU - Paddon-Row, Michael N.

AU - Sherburn, Michael S.

PY - 2007

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AB - (Chemical Equation Presented) On a short fuse: Highly stereoselective and atom-efficient domino Diels-Alder/ lactonization/Diels-Alder sequences can be carried out using simple chiral [3]dendralenes to form fused-ring systems. This short and general approach to cross-conjugated systems promotes the rapid assembly of enantiomerically pure polycyclic ring systems common to biologically interesting terpenoids with virtually complete stereocontrol (see scheme).

KW - Cross-coupling

KW - Cycloaddition

KW - Dendralenes

KW - Domino reactions

KW - Fused-ring systems

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DO - 10.1002/anie.200603335

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Chiral dendralenes for rapid access to enantiomerically pure polycycles

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