Organic letters

Synthesis of the C3-C18 Fragment of Amphidinolides G and H

AF Petri, JS Schneekloth, AK Mandal, CM Crews

Index: Petri, Andreas F.; Schneekloth Jr., John S.; Mandal, Amit K.; Crews, Craig M. Organic Letters, 2007 , vol. 9, # 16 p. 3001 - 3004

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Citation Number: 26

Abstract

A synthesis of an amphidinolides G and H C3-C18 subunits is reported. The C10-C18 segment 4 was prepared by a Negishi cross-coupling, whereas the synthesis of the C3-C9 fragment 5 employed an asymmetric cyanosilylation as the key step. The two segments were coupled by lithiation of iodide 4 and trapping of the anion with amide 5. The allylic epoxide moiety could be synthesized from the protected anti-mesylate 22.