First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening

• Published in: Tetrahedron: asymmetry Vol. 28; no. 2; pp. 246 - 249
• Main Authors: Ramesh, Perla, Narasimha Reddy, Yarram, Narendar Reddy, Thatikonda, Srinivasu, Navuluri
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 15-02-2017
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/j.tetasy.2017.01.005

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The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8-epi-parvistone A, have been accomplished from commercially available trans-cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6S,7S,8S)-isogoniothalamin oxide.