Vitamin D-3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment

M C Clasby, D Craig, A A JaxaChamiec, J Y Q Lai, A Marsh, A M Z Slawin, A J P White, D J Williams

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The enantiospecific synthesis of the vitamin D-3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a norephedrine/dihydrocitronellic acid-derived oxazolidinone, and the intramolecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The analogous cycloaddition reaction of a trienylsulfone substrate is shown to give products having the incorrect stereochemistry for vitamin D-3 synthesis.

Original languageEnglish
Pages (from-to)4769-4802
Number of pages34
JournalTetrahedron
Volume52
Issue number13
Publication statusPublished - 25 Mar 1996

Keywords

  • STEREOCONTROLLED SYNTHESIS
  • STEREOSELECTIVE SYNTHESIS
  • GRUNDMANN KETONE
  • SYSTEM

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