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 language | English |
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Pages (from-to) | 4769-4802 |
Number of pages | 34 |
Journal | Tetrahedron |
Volume | 52 |
Issue number | 13 |
Publication status | Published - 25 Mar 1996 |
Keywords
- STEREOCONTROLLED SYNTHESIS
- STEREOSELECTIVE SYNTHESIS
- GRUNDMANN KETONE
- SYSTEM