✦ LIBER ✦

Toward the total synthesis of phorboxazole A: synthesis of an advanced C4–C32 subunit using the Jacobsen hetero Diels–Alder reaction

✍ Scribed by Ian Paterson; Chris A. Luckhurst

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 242 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00754-8

No coin nor oath required. For personal study only.

✦ Synopsis

The tetrahydropyranone 3, representing a pentacyclic C 4 -C 32 segment of the phorboxazoles, was obtained by a complex hetero Diels-Alder (HDA) coupling performed between the 2-siloxydiene 23 and the oxazole aldehyde 4, mediated by the chiral tridentate Cr(III) catalyst 14. In preliminary studies, the tetrahydropyrans 17, 33 and 35 were accessed using this same asymmetric HDA methodology with varying stereoselectivity.

📜 SIMILAR VOLUMES

Toward the Total Synthesis of Phorboxazo

Toward the Total Synthesis of Phorboxazole A: Synthesis of an Advanced C4—C32 Subunit Using the Jacobsen Hetero Diels—-Alder Reaction.

✍ Ian Paterson; Chris A. Luckhurst 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 65 KB 👁 1 views

ChemInform Abstract: Towards the Total S

ChemInform Abstract: Towards the Total Synthesis of Phorboxazoles A and B: Stereocontrolled Synthesis of a C20—C32 Subunit.

✍ I. PATERSON; E. A. ARNOTT 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

Asymmetric synthesis of the C-26-C-32 te

Asymmetric synthesis of the C-26-C-32 tetrahydropyran — moiety of Swinholide A by hetero-Diels-Alder reaction

✍ Johann Mulzer; Frank Meyer; Jürgen Buschmann; Peter Luger 📂 Article 📅 1995 🏛 Elsevier Science 🌐 French ⚖ 189 KB

ChemInform Abstract: Synthetic Studies T

ChemInform Abstract: Synthetic Studies Toward Phorboxazole A. Stereoselective Synthesis of the C3—C19 and C20—C32 Subunits.

✍ David R. Williams; Michael P. Clark; Martin A. Berliner 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 1 views

Synthetic studies toward phorboxazole A.

Synthetic studies toward phorboxazole A. Stereoselective synthesis of the C3C19 and C20C32 subunits

✍ David R Williams; Michael P Clark; Martin A Berliner 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 250 KB

A stereocontrolled synthesis of two fragments comprising the macrocyclic core of Phorboxazole A is described. The C3-C19 bis-pyran segment is prepared utilizing reiterative enantioselective allylations from homochiral aUylstannanes followed by stereoselective cyclizations. The pentasubstituted tetra

Hetero-Diels–Alder Reaction with Thiazol

Hetero-Diels–Alder Reaction with Thiazolyl Oxabutadienes—Model Studies Toward the Synthesis of Directly Linked C-Disaccharide

✍ Prof. Dr. Alessandro Dondoni; Prof. Dr. Ladislav Kniezo; Dr. Miroslava Martinkov 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 English ⚖ 854 KB