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Paper | Special issue | Vol 86, No. 1, 2012, pp.219-231
Published online, 1st May, 2012
DOI: 10.3987/COM-12-S(N)3
Formal Synthesis of Hapalindole O and Synthetic Efforts towards Hapalindole K and Ambiguine A

Ryan J. Rafferty and Robert M. Williams*

*Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, U.S.A.

Abstract

he formal synthesis of D,L-hapalindole O has been accomplished intercepting Natsume’s total synthesis route. The intercepted substrate was synthesized in an overall 36% yield over ten-synthetic steps compared to Natsume’s overall 1% yield over eighteen-synthetic steps. In addition, advanced substrates for the continuing progress towards hapalindole K and ambiguine A has been synthesized. All routes described herein employ a silyl ether-based strategy accessing the functionalized 6:5:6:6 ring system, that has previously been used in our laboratory to access the total synthesis of D,L-hapalindoles J and U.