Studies towards the Total Synthesis of (–)-Caulerpenynol, a Toxic Sesquiterpenoid of the Green Seaweed Caulerpa taxifolia†

The first diastereoselective synthesis of the antimicrobial and cytotoxic agent (–)-caulerpenynol (2) was achieved in relatively few steps from commercially available (S)-malic acid. Highlights of this synthesis include the nonracemization of the sensitive α-hydroxy ketone moiety and the proper choice of the protecting groups for critical last deprotection step. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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