Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone

Amy E Hayden; Hao Xu; K C Nicolaou; K N Houk

doi:10.1021/ol060917o

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Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone

Journal article

Peer reviewed

Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone

Amy E Hayden, Hao Xu, K C Nicolaou and K N Houk

Organic letters, Vol.8(14), pp.2989-2992

07/06/2006

DOI: https://doi.org/10.1021/ol060917o

PMID: 16805534

Abstract

Polycyclic Compounds - chemistry

Polycyclic Compounds - chemical synthesis

Molecular Conformation

Crystallography, X-Ray

Alkenes - chemical synthesis

Alkenes - pharmacokinetics

Spiro Compounds - pharmacokinetics

Alkenes - chemistry

Polycyclic Compounds - pharmacokinetics

Bridged-Ring Compounds - chemistry

Spiro Compounds - chemical synthesis

Molecular Structure

Bridged-Ring Compounds - chemical synthesis

Bridged-Ring Compounds - pharmacokinetics

Spiro Compounds - chemistry

[reaction: see text] Quantum mechanical calculations demonstrate that the second step of a Claisen-Diels-Alder reaction cascade controls regioselectivity that gives advanced intermediates for the synthesis of gambogin and 1-O-methyllateriflorone.

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Title: Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone
Creators: Amy E Hayden - Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA
Hao Xu
K C Nicolaou
K N Houk
Publication Details: Organic letters, Vol.8(14), pp.2989-2992
Identifiers: 9924013703901921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone

Abstract

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