Synthetic studies relevant to biosynthetic research on vitamin B12. Part 11. Modification of the east and west building blocks and study of different assembly methods for synthesis of isobacteriochlorins

Alan R. Battersby, Michael H. Block, Finian J. Leeper, Steven C. Zimmerman

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The eastern and western building blocks required for the photochemical route to isobacteriochlorins have been synthesized by a C-C bond-forming step which leaves a cyano group on the bridge carbon, e.g. 5. Two methods have been developed to remove this cyano residue which use retro-Mannich reactions to eliminate either an aminomethyl group, resulting from reduction of the nitrile, or the corresponding sulfonamido group. Two effective ways to carry out the final steps of the isobacteriochlorin synthesis have also been developed.

Original languageEnglish
Pages (from-to)2189-2195
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
DOIs
StatePublished - 1 Jan 1992
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry

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