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

53 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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title = "Chiral dendralenes for rapid access to enantiomerically pure polycycles",

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",

doi = "10.1002/anie.200603335",

language = "English",

volume = "46",

pages = "937--940",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons Ltd.",

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T1 - Chiral dendralenes for rapid access to enantiomerically pure polycycles

AU - Miller, Natalie A.

AU - Willis, Anthony C.

AU - Paddon-Row, Michael N.

AU - Sherburn, Michael S.

PY - 2007

Y1 - 2007

N2 - (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).

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

UR - https://www.scopus.com/pages/publications/33846686864

U2 - 10.1002/anie.200603335

DO - 10.1002/anie.200603335

M3 - Article

SN - 1433-7851

VL - 46

SP - 937

EP - 940

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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