Assembly of the Entire Carbon Backbone of a Stereoisomer of the Antitumor Marine Natural Product Hemicalide

• Published in: Chemistry : a European journal Vol. 25; no. 11; pp. 2745 - 2749
• Main 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
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.02.2019; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Subjects: Aldehydes; Assembly; Backbone; Carbon; Chemical Sciences; Chemistry; Chemistry, Multidisciplinary; hemicalide; multistep synthesis; Natural products; Organic chemistry; Physical Sciences; polyketides; Science & Technology; stereochemistry; Stereoisomers; MEDIATED ALDOL REACTIONS; hemicalide; ALDEHYDES; polyketides; DISCOVERY; natural products; REDUCTION; stereochemistry; ASSIGNMENT; FRAGMENT; multistep synthesis; STEREOSELECTIVE-SYNTHESIS; METHYL KETONES; DELTA-LACTONES
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201806327

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. 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.