[Show abstract][Hide abstract] ABSTRACT: A highly convergent synthesis of the C9-C28 spiroacetal subunit of didemnaketal B has been accomplished. Assembly of the C9-C15 alkylborate and C16-C21 enol phosphate by means of Suzuki-Miyaura coupling and acid-catalyzed cyclization of the derived dihydroxy enol ether enabled a rapid and efficient construction of the spiroacetal subunit. The C22-C28 side chain was incorporated via Nozaki-Hiyama-Kishi coupling to complete the synthesis.
[Show abstract][Hide abstract] ABSTRACT: A stereocontrolled convergent synthesis of a DEFG-ring model compound of gambieric acids, highly potent antifungal marine polycyclic ether natural products, has been achieved based on Suzuki-Miyaura coupling. Conformational analysis of the model compound revealed that the nine-membered F-ring exists exclusively as a single stable conformer, as opposed to that of ciguatoxins.
No preview · Article · Aug 2010 · The Journal of Organic Chemistry
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[Show abstract][Hide abstract] ABSTRACT: A stereocontrolled entry to the DEFG-ring skeleton of gambieric acids, potent antifungal polycyclic ether natural products, has been developed based on the Suzuki–Miyaura coupling as the fragment assembly process and the use of an oxepane as a template for controlling the C25 stereogenic center.
No preview · Article · Jan 2009 · Chemistry Letters