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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: 120
Category: Article
ISSN: 0044-8249
DOI: 10.1002/ange.200890007

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Total Synthesis of (+)-Aquaticol by Biom

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

✍ Julien Gagnepain; Frederic Castet; Stephane Quideau 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 15 KB

Total Synthesis of (+)-Aquaticol by Biom

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

✍ Julien Gagnepain; Frédéric Castet; Stéphane Quideau 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 129 KB

Total Synthesis of (+)-Aquaticol by Biom

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

✍ Julien Gagnepain; Frédéric Castet; Stéphane Quideau 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 130 KB

Total Synthesis of (+)-Aquaticol by Biom

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

✍ Julien Gagnepain; Frédéric Castet; Stéphane Quideau 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 English ⚖ 208 KB

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