The Journal of Organic Chemistry

Syntheses of some proposed biosynthetic precursors to the isocyclic ring in chlorophyll a

KM Smith, DA Goff

Index: Smith, Kevin M.; Goff, Dane A. Journal of Organic Chemistry, 1986 , vol. 51, # 5 p. 657 - 666

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Citation Number: 6

Abstract

In connection with studies on the biosynthesis of the isocyclic ring E in chlorophyll a (l), the magnesium (I1) 2, 4divinylporphyrin 0-keto ester 8 and hydroxypropionate 6 have been synthesized. The key porphyrin intermediate 36 in these syntheses was obtained most efficiently by cyclization of a l'-methyl-8'-unsubstituted a, c-biladiene dihydrobromide 31 in hot o-dichlorobenzene. An alternative route through copper (I1)-promoted cyclization of a ...