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A convergent total synthesis of (+)-anamarine from (R,R)-tartrate and D-gulonolactone

✍ Scribed by Klaus Lorenz; Frieder W. Lichtenthaler


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
277 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis


The (R R)-6-alkoxy-2-triphenylphosphoniomethyl-dihydropyran iodide 2 and the --di-acetonide of 6-deoxy-aldehydo-L-glucose 3 are elaborated from (R,R)-tartrate and D-gulonolactone, resp., and subsequently joined to yield (+)-anamarine (l), identical with the Hyptis-derived product.


πŸ“œ SIMILAR VOLUMES


A convergent total synthesis of (βˆ’)-anam
✍ Frieder W Lichtenthaler; Klaus Lorenz; Wei-yong Ma πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 290 KB

The di-acetonide of 6-deoxy-aLdehydo-D-qlucose Lz and (S,S)-2-ethoxy-6-triphenylphosphoniomethyl-dihydropyran iodide 2 are elaborated from D-glucose each in practicable procedures of 5 and 10 steps, resp., and subsequently joined to give, after oxidation, deprotection and acetylation, (-I-anamarine

Enantioselective total synthesis of (R)-
✍ Stefan Reber; Thomas F KnΓΆpfel; Erick M Carreira πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 145 KB

We describe an expeditious enantioselective total synthesis of the acetylenic marine natural products (R)-strongylodiols A and B. Central to the strategy is the use of Zn(OTf) 2 , amine base, and N-methyl ephedrine to mediate the direct addition of a 1,3-diyne to two longchain aliphatic aldehydes in