152458-98-5Relevant articles and documents
Vitamin D3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment
Clasby, Martin C.,Craig, Donald,Jaxa-Chamiec, Albert A.,Lai, Justine Y. Q.,Marsh, Andrew,Slawin, Alexandra M. Z.,White, Andrew J. P.,Williams, David J.
, p. 4769 - 4802 (1996)
The enantiospecific synthesis of the vitamin D3 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 D3 synthesis.