Organometallics in organic synthesis. Applications of a new diorganozinc reaction to the synthesis of C-glycosyl compounds with evidence for an oxonium-ion mechanism

Alan P. Kozikowski, Toshiro Konoke, Allen Ritter

Research output: Contribution to journalArticlepeer-review

Abstract

The mechanistic and stereochemical features of a new organozinc-based substitution process [heteroatom-C-(R1,R2)-SPh + R32Zn → heteroatom-C-(R1,R2,R3)], first discovered during a total synthesis of the alkaloid mycotoxin α-cyclopiazonic acid, are described. Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process. Since these sulfur compounds are converted into C-glycosyl compounds with some degree of stereoselectivity, the organozinc chemistry does provide a new entry to these biologically active substances.

Original languageEnglish (US)
Pages (from-to)109-124
Number of pages16
JournalCarbohydrate Research
Volume171
Issue number1
DOIs
StatePublished - Dec 1 1987

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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