Optically Active Allenes from β-Lactone Templates:  Asymmetric Total Synthesis of (-)-Malyngolide

Zhonghui Wan and Scott G. Nelson*

*Department of Chemistry University of Pittsburgh Pittsburgh, Pennsylvania 15260, Email: sgnelsonpitt.edu

Z. Wan, S. G. Nelson, J. Am. Chem. Soc., 2000, 122, 10470-10471.

DOI: 10.1021/ja002783u

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Abstract

An asymmetric AAC-S_N2' ring opening sequence provides an efficient and operationally simple synthesis of di and trisubstituted enantiomeric allene derivatives. A highly efficient enantioselective synthesis of the naturally occurring antibiotic malyngolide highlights the utility of these allene derivatives in asymmetric organic synthesis.

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Malyngolide retrosynthesis

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Key Words

allenes

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ID: J48-Y2000