𝔖 Bobbio Scriptorium
✦   LIBER   ✦

First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol

✍ Scribed by Gerhard Bringmann; Thomas Pabst; David S. Rycroft; Joseph D. Connolly

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
206 KB
Volume
40
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The first synthesis of mastigophorenes A and B by oxidative phenolic coupling of partially protected derivatives of their joint natural monomeric half, herbertenediol, is described. The synthesis starts from this diol itself or from the corresponding aldehyde, both available by isolation from the liverwort, Herbertus aduncus. After transformation of herbertenediot to a chemically appropriate monophenolic coupling precursor, the oxidative dehydrodimerization was brought about using (ten-BuO)z, followed by deprotection to give mastigophorenes A and B in their 'natural' atropisomeric ratio, as isolated from the liverwort.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Novel Concepts in D
ChemInform Abstract: Novel Concepts in Directed Biaryl Synthesis. Part 76. First Synthesis of Mastigophorenes A and B, by Biomimetic Oxidative Coupling of Herbertenediol.
✍ Gerhard Bringmann; Thomas Pabst; David S. Rycroft; Joseph D. Connolly πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 29 KB πŸ‘ 2 views

Novel Concepts in Directed Biaryl Synthesis. Part 76. First Synthesis of Mastigophorenes A and B, by Biomimetic Oxidative Coupling of Herbertenediol. -The first synthesis of the title compounds (I), which are atropisomers, by oxidative phenolic coupling of partially protected derivatives of their j

Synthesis of (-)-herbertenediol and (aR,
Synthesis of (-)-herbertenediol and (aR, aS)-mastigophorenes A via asymmetric intramolecular heck coupling reaction
✍ Ai-Min Zhang; Guo-Qiang Lin πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons 🌐 English βš– 575 KB

## Abstract Total enantioselective synthesis of the natural (‐)‐Herbertenediol (1) was accomplished in eleven steps with an overall yield of 15% starting from the 2‐methoxy‐4‐methyl‐phenol. The total synthesis features asymmetric intramolecular Heck reaction and Wolff‐Kishner‐Huang reduction. (a__R

ChemInform Abstract: Total Syntheses of
ChemInform Abstract: Total Syntheses of (-)-Herbertenediol (I), (-)-Mastigophorene A (II), and (-)-Mastigophorene B (III). Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines.
✍ Andrew P. Degnan; A. I. Meyers πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 27 KB πŸ‘ 2 views

Total Syntheses of (-)-Herbertenediol (I), (-)-Mastigophorene A (II), and (-)-Mastigophorene B (III). Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines.