Journal
TETRAHEDRON
Volume 63, Issue 26, Pages 5977-6003Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.02.039
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A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring. (C) 2007 Elsevier Ltd. All rights reserved.
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