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

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

Org Lett. 2006 Jul 6;8(14):2989-92. doi: 10.1021/ol060917o.

Authors

Amy E Hayden¹, Hao Xu, K C Nicolaou, K N Houk

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

PMID: 16805534
DOI: 10.1021/ol060917o

Abstract

[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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Alkenes / pharmacokinetics
Bridged-Ring Compounds / chemical synthesis*
Bridged-Ring Compounds / chemistry
Bridged-Ring Compounds / pharmacokinetics
Crystallography, X-Ray
Molecular Conformation
Molecular Structure
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry
Polycyclic Compounds / pharmacokinetics
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Spiro Compounds / pharmacokinetics

Substances

Alkenes
Bridged-Ring Compounds
Polycyclic Compounds
Spiro Compounds
gambogin
lateriflorone