Total Synthesis of Soraphen A1α

Stephan Abel; Dominik Faber; Ottmar Hüter; Bernd Giese

doi:10.1055/s-1999-3671

Synthesis 1999; 1999(1): 188-197
DOI: 10.1055/s-1999-3671

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Total Synthesis of Soraphen A_1α

Stephan Abel^* , Dominik Faber, Ottmar Hüter, Bernd Giese

^*Institut für Organische Chemie, Universität Basel, St. Johanns Ring 19, CH-4056 Basel, Switzerland; Fax +41(61)2 67 11 05; E-mail: giese@ubaclu.unibas.ch

Abstract

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The convergent synthesis of macrolide soraphen A_1α is described starting from glucose (western part) and mannose (eastern part). Mannose was converted into a 2-deoxyribohexapyranoside that could be methylated and reduced stereoselectively. Chain elongation at C-6 was carried out by stereoselective addition of a magnesium acetylide. The two fragments (western and eastern) were assembled by a Julia olefination followed by macrolactonization. The introduction of the methyl group at C-2 of norsoraphen occurred stereoselectively for thermodynamic reasons.

Soraphen A_1α - macrolide - Julia olefination - chiral pool

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