Assembly of the Entire Carbon Backbone of a Stereoisomer of the Antitumor Marine Natural Product Hemicalide. Issue 11 (25th January 2019)

• Record Type: Journal Article
• Authors: Lecourt, Camille; Dhambri, Sabrina; Yamani, Khalil; Boissonnat, Guillaume; Specklin, Simon; Fleury, Etienne; Hammad, Karim; Auclair, Eric; Sablé, Serge; Grondin, Antonio; Arimondo, Paola B.; Sautel, François; Massiot, Georges; Meyer, Christophe; Cossy, Janine; Sorin, Geoffroy; Lannou, Marie‐Isabelle; Ardisson, Janick
• Is Part Of: Chemistry. Volume 25:Issue 11(2019)
• Page Start: 2745
• Page End: 2749
• Publication Date: 2019-01-25
• Subjects: hemicalide -- multistep synthesis -- natural products -- polyketides -- stereochemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201806327
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A strategy for the assembly of the entire carbon backbone of a stereoisomer of the antitumor marine natural product hemicalide has been investigated. The devised convergent approach relies on Horner–Wadsworth–Emmons and Julia–Kocienski olefination reactions for the construction of the C6=C7 and C34=C35 double bonds, respectively, an aldol reaction to create the C27−C28 bond, and a Suzuki–Miyaura cross‐coupling as the endgame to form the C15−C16 bond. Abstract : A strategy for the assembly of the entire carbon backbone of a stereoisomer of the antitumor marine natural product hemicalide has been investigated. The devised convergent approach relies on Horner–Wadsworth–Emmons and Julia–Kocienski olefination reactions for the construction of the C6=C7 and C34=C35 bonds, respectively, an aldol reaction to create the C27−C28 bond, and a Suzuki–Miyaura cross‐coupling as the endgame to form the C15−C16 bond.