Total Synthesis of (+)-Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a C2-Symmetric Transition State

✍ Scribed by Julien Gagnepain; Frédéric Castet; Stéphane Quideau

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 208 KB
• Volume: 47
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200890007

✦ Synopsis

The absolute configuration of (þ)-aquaticol (1 a) described in this Communication should be revised to 3S,10S,14R,23R as shown on the structure below and its accompanying ORTEP diagram (monoclinic, P2 1 , Flack factor = À0.2(2), CCDC-295794). (þ)-Aquaticol was derived from SIBX-mediated oxidation of (þ)-(R)hydroxycuparene (3). We