Tetrahedron letters

A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1, 2-dioxolane group

AJ Bloodworth, BD Bothwell, AN Collins, NL Maidwell

Index: Bloodworth; Bothwell, Brian D.; Collins, Andrew N.; Maidwell, Nicola L. Tetrahedron Letters, 1996 , vol. 37, # 11 p. 1885 - 1888

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Citation Number: 30

Abstract

Natural and unnatural analogues 4 of plakinic acids A, C and D have been prepared in three steps from alkan-2-ones by (i) LDA-induced condensation with ethyl 3-methylbut-2-enoate to give (2Z)-3, 5-dimethylalka-2, 4-dienoic acids 10, then (ii) isomerisation to the 2E-isomers 5 and finally (iii) peroxymercuriation with 30% hydrogen peroxide and reduction in situ with sodium borohydride.