Synthetic Studies towards Pectenotoxin??2: Synthesis of the Nonanomeric 10??epi??ABCDE Ring Segment by Kinetic Spiroketalization

JE Aho, A Piisola, K Syam Krishnan…

Index: Aho, Jatta E.; Piisola, Antti; Syam Krishnan; Pihko, Petri M. European Journal of Organic Chemistry, 2011 , # 9 p. 1682 - 1694

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Citation Number: 7

Abstract

Abstract The synthesis of the nonanomeric 10-epi-ABCDE ring system of pectenotoxin-2 has been achieved by using a kinetic spiroketalization reaction. The synthesis of the spiroketalization precursor was achieved through a cross-metathesis/hydrogenation sequence. The formation of the epi-C10 isomer resulted from an unexpected anti-Felkin selective addition of organometallic nucleophiles to the advanced CDE ring precursor. ...