Biomimetic synthesis of (-)-longithorone A

Mark E Layton; Carl A Morales; Matthew D Shair

doi:10.1021/ja016585u

Biomimetic synthesis of (-)-longithorone A

J Am Chem Soc. 2002 Feb 6;124(5):773-5. doi: 10.1021/ja016585u.

Authors

Mark E Layton¹, Carl A Morales, Matthew D Shair

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138,USA.

PMID: 11817951
DOI: 10.1021/ja016585u

Abstract

An enantioseletive, biomimetic synthesis of (-)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer control during ene-yne metathesis macrocyclizations.

Publication types

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

MeSH terms

Biological Factors / chemical synthesis*
Bridged-Ring Compounds / chemical synthesis*
Molecular Mimicry
Polycyclic Compounds / chemical synthesis*
Stereoisomerism

Substances

Biological Factors
Bridged-Ring Compounds
Polycyclic Compounds
longithorone A