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A Formal Total Synthesis of (±)-Halichlorine and (±)-Pinnaic Acid

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journal contribution
posted on 18.03.2004, 00:00 by Yosuke Matsumura, Sakae Aoyagi, Chihiro Kibayashi
A stereocontrolled approach for the preparation of the Danishefsky intermediates has been developed starting with the azaspirobicyclic ketone as a common precursor, representing a formal total synthesis of (±)-halichlorine and (±)-pinnaic acid. This approach involves the construction of the 1,7-disubstituted 6-azaspiro[4.5]decane with the proper stereochemistry established by olefin hydrogenation followed by C-methylation of the spirotricyclic lactam and the subsequent processes involving lactam ring-opening using methyl triflate and RCM to form the azaspirotricyclic quinolizidine skeleton.

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