Tetrahedron Letters p. 4365 - 4368 (1993)
Update date:2022-09-26
Topics:
Deroose, Frederik D.
Clercq, Pierre J. De
A conceptually simple enantioselective 14-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cyclodaddition sequence involving (i) elimination of bromide 8 to the endocyclic thioenol ether 9, (ii) thermolysis of the ene carbamoyl azide 9 to the exocyclic thioenol ether 10.Both the synthesis of 8 and the final transformation of 10 into (+)-biotin are based upon literature precedents.
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