Tetrahedron letters

Studies on the substituted 3-aminopropan-1-ol motif of lycoctonine class norditerpenoid alkaloids: A novel route to 3-hydroxymethylcyclohex-2-enone

X Doisy, IS Blagbrough, NF Thomas, BVL Potter

Index: Doisy, Xavier; Blagbrough, Ian S.; Thomas, Noel F.; Potter, Barry V. L. Tetrahedron Letters, 1998 , vol. 39, # 46 p. 8525 - 8528

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Abstract

Pursuing our interest in methyllycaconitine (MLA), we have designed a synthetic route to substituted ring-A of lycoctonine class norditerpenoid alkaloids. A novel synthesis of 3- hydroxymethylcyclohex-2-enone has been achieved starting from cyclohex-2-enone. Key reactions are: 1, 2-addition of 1, 3-dithiane followed by allylic rearrangement, 1, 4- hydrocyanation, Wittig reaction and conversion into the substituted N-ethyl-3- ...

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