Unexpected Rearrangement in the Peroxytrifluoroacetic Acid-Mediated Baeyer-Villiger Oxidation of trans-3.beta.-Hydroxy-4,4,10.beta.-trimethyl-9-decalone Forming a 7-Oxabicyclo[2.2.1]heptane. Structure Proof and Total Synthesis of (.+-.)-Farnesiferol-C

1995 ◽  
Vol 60 (16) ◽  
pp. 5114-5120 ◽  
Author(s):  
F. W. Joachim Demnitz ◽  
Cristiane Philippini ◽  
Ralph A. Raphael
Keyword(s):  
Total Synthesis ◽  
Villiger Oxidation

Alkaloids from alkaloids: total synthesis of (±)-7a-epi-hyacinthacine A1 from Z-protected tropenone via Baeyer–Villiger oxidation

Tetrahedron ◽  
2009 ◽  
Vol 65 (33) ◽  
pp. 6626-6634 ◽  
Author(s):  
Olena Affolter ◽  
Angelika Baro ◽  
Wolfgang Frey ◽  
Sabine Laschat
Keyword(s):  
Total Synthesis ◽  
Villiger Oxidation

ChemInform Abstract: Total Synthesis of a Monocyclofarnesane Norsesquiterpenoid Isolated from Mushroom Ingested by Beetle: Utility of Solid State Baeyer-Villiger Oxidation.

ChemInform ◽  
2010 ◽  
Vol 30 (30) ◽  
pp. no-no
Author(s):  
Hisahiro Hagiwara ◽  
Hidenori Nagatomo ◽  
Shin-ichi Kazayama ◽  
Hitoshi Sakai ◽  
Takashi Hoshi ◽  
...  
Keyword(s):  
Solid State ◽  
Total Synthesis ◽  
Villiger Oxidation

A selective baeyer-villiger oxidation: A total synthesis of (−)-Acetomycin

1993 ◽  
Vol 34 (48) ◽  
pp. 7669-7672 ◽  
Author(s):  
Frederick E. Ziegler ◽  
Hakwon Kim
Keyword(s):  
Total Synthesis ◽  
Villiger Oxidation

Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: utility of solid state Baeyer–Villiger oxidation

1999 ◽  
pp. 457-460 ◽  
Author(s):  
Hisahiro Hagiwara ◽  
Hidenori Nagatomo ◽  
Shin-ichi Kazayama ◽  
Hitoshi Sakai ◽  
Takashi Hoshi ◽  
...  
Keyword(s):  
Solid State ◽  
Total Synthesis ◽  
Villiger Oxidation

Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol

2021 ◽  
Author(s):  
Xiangtao Chen ◽  
Lei Yu ◽  
huijing Wang ◽  
Wen Zhang ◽  
Pei Tang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Different Types ◽  
Synthetic Work ◽  
Villiger Oxidation

A concise stereoselective total synthesis of (±)-vindeburnol and its epimer (±)-16-epi-vindeburnol is presented. This synthetic work features the utilization of Baeyer-Villiger oxidation to install different types of lactone substrate, and...

A convenient entry into the rhoeadan skeleton. Total synthesis of (±) cis-alpinigenine

1982 ◽  
Vol 60 (21) ◽  
pp. 2678-2686 ◽  
Author(s):  
Ijaz Ahmad ◽  
Victor Snieckus
Keyword(s):  
Total Synthesis ◽  
Polyphosphoric Acid ◽  
Chromium Trioxide ◽  
Total Syntheses ◽  
Diisobutylaluminum Hydride ◽  
Hydride Reduction ◽  
Villiger Oxidation ◽  
Parallel Series

Condensation of 4-bromoisochroman-3-one (8a) with N-methyl-3,4-dimethoxy-β-phenethylamine (7) provides the aminolactone 9a which by diisobutylaluminum hydride reduction followed by polyphosphoric acid mediated cyclization gives the tetracyclic product 10a, thus constituting a convergent, short entry into the rhoeadan alkaloid skeleton. Chromium trioxide oxidation of 10a affords a low yield of the corresponding lactone 11a. A parallel series of reactions starting from 7,8-dimethoxy-4-bromoisochroman-3-one (8b), prepared either via Baeyer–Villiger oxidation of 4,5-dimethoxy-2-indanone (14) or, more conveniently, via benzeneboronic acid assisted condensation of 3-hydroxy-4-methoxyphenylacetic acid (18) with formaldehyde, yields 7,8,12,13-tetramethoxy-3-methylrhoeadan (10b). Oxidation of compound 10b with chromium trioxide gives the corresponding lactone 11b also in low yield. Since 11b has been previously converted into (±)-cis-alpinigenine (11c) and (±)-cis-alpinine(11d), this work constitutes total syntheses of these alkaloids.

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