Formal total synthesis of erythromycin A. Part II. Preparation of a 1,7-dioxaspiro[5.5]undecane derivative of erythronolide A seco acid methyl ester from erythromycin A

Bruno Bernet,Paul M. Bishop,Maurice Caron,Takeshi Kawamata,Bernard L. Roy,Luc Ruest,Gilles Sauvé,Pierre Soucy,Pierre Deslongchamps

Formal total synthesis of erythromycin A. Part II. Preparation of a 1,7-dioxaspiro[5.5]undecane derivative of erythronolide A seco acid methyl ester from erythromycin A

1985

Bruno Bernet
Paul M. Bishop
Maurice Caron
Takeshi Kawamata
Bernard L. Roy
Luc Ruest
Gilles Sauvé
Pierre Soucy
Pierre Deslongchamps

Degradation of erythromycin A gives spirocompound 18A. Compound 18A is then converted into the spirolactone 22 via 21. Compound 21 is then reconverted into spiro product 18A.

Keywords:

Total synthesis
Organic chemistry
Spirolactone
Erythromycin
Lactone
Undecane
Bicyclic molecule
Stereochemistry
Chemical decomposition
Chemistry
Acetal

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