Studies on the Synthesis of Landomycin A. Synthesis of the
Originally Assigned Structure of the Aglycone, Landomycinone,
and Revision of Structure
William R. Roush
R. Jeffrey Neitz
10.1021/jo049426c.s001
https://acs.figshare.com/articles/journal_contribution/Studies_on_the_Synthesis_of_Landomycin_A_Synthesis_of_the_Originally_Assigned_Structure_of_the_Aglycone_Landomycinone_and_Revision_of_Structure/3331159
The originally proposed structure (<b>2</b>) of landomycinone, the aglycone of landomycin A, has been
synthesized and shown to be nonidentical to the naturally derived landomycin A aglycone. The
synthesis of <b>2</b> features the Dötz benzannulation reaction of chromium carbene <b>5</b> and alkyne <b>6</b>, and
the intramolecular Michael-type cyclization reaction of the phenolic naphthoquinone <b>20</b>. It is
proposed that natural landomycinone possesses the alternative structure <b>3</b>, but attempts to access
this structure via the Michael-type cyclization of the isomeric phenolic naphthoquinone <b>38</b> have
been unsuccessful.
2004-07-23 00:00:00
chromium carbene 5
isomeric phenolic naphthoquinone 38
cyclization
Assigned Structure
D ötz benzannulation reaction
landomycin
alternative structure 3
2 features
aglycone
phenolic naphthoquinone 20
alkyne 6
Synthesi
landomycinone