1999 nucleic acids

nucleic acidsU 0700

14 - 258Optically Active Cyclobutanone Chemistry: Synthesis of (-)-Cyclobut-A and (±)-3’-epi-Cyclobut-A. — trans-Cyclobutane (IV),obtained by removal of the ethoxy group from cyclobutane (III) with inversionof the stereocenter, is successfully elaborated to give the target title compounds.The most efficient route to desired epimer (VII) for the synthesis of (-)-cyclobut-A (XII) is a sequence of hydroboration/oxidation/epimerization/reduction withminimal purification of the intermediates. The preparation of the correspondingracemic β-hydroxymethyl epimer as precursor for 3’-epi-cyclobut-A is alsodescribed. — (BROWN, BRIAN; HEGEDUS, LOUIS S.; J. Org. Chem. 63(1998) 22, 8012-8018; Dep. Chem., Colo. State Univ., Fort Collins, CO 80523,USA; EN)

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