Asymmetric Total Synthesis of (+)-7-Deoxypancratistatin

Xinrong Tian; Rakesh Maurya; Kurt Königsberger; Tomas Hudlicky

doi:10.1055/s-1995-5221

Synlett 1995; 1995(11): 1125-1126
DOI: 10.1055/s-1995-5221

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Asymmetric Total Synthesis of (+)-7-Deoxypancratistatin

Xinrong Tian, Rakesh Maurya, Kurt Königsberger, Tomas Hudlicky^*

^*Department of Chemistry, University of Florida, Gainesville, FL 32611, USA

Abstract

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An asymmetric synthesis of 7-deoxypancratistatin 1 has been accomplished starting from diol 2 via two pathways in overall yields of 2.6 and 3.0%, respectively. The key step involved the regioselective ring opening of tosylaziridine 3 or the new carbomethoxyaziridine 15 with a higher-order cuprate and the cyclization of urethane 11.

3-Bromo-3,5-cyclohexadiene-1,2-diol - vinylaziridine - higher-order cuprate - Bischler-Napieralski cyclisation

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